Name: 112-85-6|Docosanoic acid|85%
Brand: Ambeed
SKU: A538500
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1
[ 908094-01-9 ]
[ 112-85-6 ]
[ 929-77-1 ]

Yield	Reaction Conditions	Operation in experiment
	With diethyl ether
	In Petroleum ether Acidic conditions;

Reference： [1]Dryden; Welsh [Australian Journal of Scientific Research, Series A: Physical Sciences, 1951, vol. 4, p. 616,619,623]
[2]Location in patent: body text Korobko; Turko; Shokun; Chernyak; Pokrovskii; Smetankina; Kerimzhanova; Baltaev [Chemistry of Natural Compounds, 2008, vol. 44, # 3, p. 359 - 360]

2
[ 67-56-1 ]
[ 112-85-6 ]
[ 929-77-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid
	With sulfuric acid for 7h; Heating;
	With sulfuric acid Heating;

Reference： [1]Levene; Taylor [Journal of Biological Chemistry, 1924, vol. 59, p. 921]
[2]Deshmukh; Veeresh [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 12, p. 1239 - 1241]
[3]Yildirim, Ayhan [Acta Chimica Slovenica, 2015, vol. 62, # 2, p. 473 - 478]

3
[ 64-17-5 ]
[ 112-85-6 ]
[ 5908-87-2 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1847,vol. 64,p. 342

4
[ 112-86-7 ]
[ 112-85-6 ]

Yield	Reaction Conditions	Operation in experiment
90.3%	With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; at 20 - 30℃; under 4500.45 - 6000.6 Torr;	13-Docosenoic acid (100 g) was suspended in THF (1500 ml) at 20-30C and hydrogenated in the presence of Palladium on charcoal (5 g, 10% w/w, 50 % wet) at 20-30 C over a hydrogen pressure of 6-8 Kg/cm . After completion of reaction the catalyst was filtered off, solvent was evaporated from the filtrate under reduced pressure (20-40 mm Hg) at 40-50 C to get a white colour residue. The above residue was suspended in methanol (1000 ml) and heated to 60-65C to obtain a clear solution and cooled to 20-30C slowly over a period of 30+5 min stirred for an hour at 20-30 C. The resulting solid was filtered and dried under reduced pressure (10-20 mm Hg) at 40-45 C to afford 90.83 g of Docosanoic acid. Yield: 90.3 % of theory Chromatographic purity (by GC): >98 %

Reference： [1]Patent: WO2018/220504,2018,A1 .Location in patent: Page/Page column 7; 8
[2]Patent: DE187788,
[3]Bulletin of the Chemical Society of Japan,1935,vol. 10,p. 138
Nippon Kagaku Kaishi,1935,vol. 56,p. 336
Chem.Abstr.,1935,p. 4330
[4]Journal of the American Chemical Society,1946,vol. 68,p. 231
[5]Journal of the American Chemical Society,1948,vol. 70,p. 366
[6]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1909,vol. 149,p. 999
[7]Patent: DE187788,
[8]Bulletin de la Societe Chimique de France,1889,vol. <3>1,p. 296
[9]Journal of Biological Chemistry,1915,vol. 20,p. 527
[10]Monatshefte fur Chemie,1913,vol. 34,p. 1132
[11]Journal of the American Chemical Society,1926,vol. 48,p. 971
[12]Organic Process Research and Development,2012,vol. 16,p. 1307 - 1311

5
[ 4704-94-3 ]
[ 112-85-6 ]
[ 103511-42-8 ]

Reference： [1]Chemische Berichte,1955,vol. 88,p. 1511,1516,1518

6
[ 112-85-6 ]
[ 3061-75-4 ]

Yield	Reaction Conditions	Operation in experiment
99%		To 50 mL of toluene were added 5.5 g (16.17 mmol) of behenic acid. Then, to the resulted dispersion was added dropwised 10.26 g (80.78 mmol) of oxalyl chloride and the complete mixture was stirred refluxing for 2 h under argon atmosphere. The solvent and unreacted reagents were both removed under reduced pressure to produce colored oil which was introduced in 50 mL of THF without further purification. In the next step, 20 mL of 25% NH4OH aqueous solution was added to the previous clear yellow solution and a white solid started to precipitate which was successively filtrated on Buchner, washed with a slight volume of water and THF (mass=5.43 g; yield=99%). The recovered behenamide powder was dried in a dessicator and remained insoluble in common organic solvents. FT-IR: 3396cm-1 (NH); 2849-2916cm-1 (CH2); 1647 and 1526cm-1 (amide). MS: Calcd (M+H+) 339 found 339.23.
98.7%	With ammonia; zircornium(IV) n-propoxide; at 165℃; for 7h;	General procedure: According to the embodiment of the present invention described above, stearic acid amide, which is a kind of carboxylic acid amide compound, was prepared in Example 1 as follows. First, the carboxylic acid injector 250 injects 1000 g of stearic acid into the heater 100, and the heater 100 heats 1000 g of stearic acid to 120 C. Subsequently, when stearic acid is injected into the first reaction tank 210, the first catalyst injector 261 injects 10 g of tetraisopropyl titanium, which is a metal catalyst, into the first reaction tank 210, Was heated by the heater attached to the first reaction tank 210. When 150 g of stearic acid was charged into the first reaction tank 210, the first ammonia injector 281 started to feed the ammonia gas through the ammonia pipe 283 at a rate of 100 L / hr. When 500 g of stearic acid was charged into the first reaction tank 210, the introduction of stearic acid into the first reaction tank 210 was stopped. The propeller in the first reaction tank 210 was mixed with stearic acid and ammonia while maintaining the reaction temperature at 165 C in the first reaction tank 210.Next, when the supply of the stearic acid to the first reaction tank 210 is stopped, the 500 g of stearic acid remaining in the heater 100 through the valve is changed to be supplied to the second reaction tank 220. When stearic acid is injected into the second reaction tank 220, the second catalyst injector 262 injects 10 g of tetraisopropyl titanium as a metal catalyst into the second reaction tank 220 and starts heating the second reaction tank 220 . When 150 g of stearic acid was charged into the second reaction tank 220, the second ammonia feeder 282 started to feed the ammonia gas through the ammonia pipe 283 at a rate of 100 L / hr. When all 500 g of stearic acid was fed to the second reaction tank, the addition of stearic acid to the second reaction tank was stopped. The propeller in the second reaction tank 220 was mixed with stearic acid and ammonia while maintaining the reaction temperature of 165 C in the second reaction tank 220.In Examples 2 to 10, other carboxylic acid amide compounds were prepared in the same manner as in Example 1, except that stearic acid was used instead of stearic acid and other carboxylic acids as shown in the following Table 1 as "acid".

Reference： [1]Journal of Molecular Liquids,2020,vol. 303
[2]Patent: KR101678461,2016,B1 .Location in patent: Paragraph 0059-0062; 0076
[3]Gazzetta Chimica Italiana,1893,vol. 23 II,p. 392
Gazzetta Chimica Italiana,1897,vol. 27 II,p. 298
[4]Journal of Physical Chemistry,1993,vol. 97,p. 12848 - 12857
[5]Analytical Chemistry,2012,vol. 84,p. 2388 - 2394

7
[ 112-85-6 ]
[ 21132-76-3 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In benzene;	EXAMPLE 28 A mixture of docosanoic acid (500 mg) and thionyl chloride (2 ml) in benzene (5 ml) was refluxed for 1 hour. After removal of the solvent under reduced pressure, the residue was taken up in benzene and benzene was evaporated off. This operation was repeated three times to give crude docosanoyl chloride.
	With thionyl chloride; at 45℃; for 1.66667h;	In a dry 2-necked, round bottomed flask, equipped with a magnetic stirrer and fixed with a separatory funnel, containing 7.88 ml (108 mmol) of thionyl chloride, and a water condenser, is placed 20.44 g (60 mmol) of docosanoic acid. Addition of the thionyl chloride is completed with heating to about 45 C. over the course of about 30 minutes. When addition of the thionyl chloride is complete the mixture is heated and stirred for an additional 70 minutes. The water condenser is then replaced with a distillation side arm condenser and the crude mixture is distilled. The crude distillate in the receiving flask is then fractionally distilled to obtain the acyl chloride, docosanoyl chloride. This acyl chloride, 21.60 g (60 mmol), is put into a dry separatory funnel and combined with 100 ml of dry dichloromethane for use in the next step of the reaction.
	With thionyl chloride; In dichloromethane; for 4h;Heating / reflux;	[208] Example 1 : Preparation of 4-docosanoyl-l,l-dimethylpiperazin-l-ium iodide according to Reaction Scheme 1; [209] 1. Preparation of l-(4-methylpiperazine-l-v0docosan-l-one; [210][211] Thionyl chloride (0.43 D, 5.86 mmol) was added to a 0.1 M methylene chloride solution of docosanoic acid (1 g, 2.93 mmol) under stirring, and heated for 4 hours. The produced mixture was cooled to room temperature, and then methylpiperazine (1.30 D, 11.72 mmol) was added thereto at O0C under stirring for 2 hours. The produced mixture was diluted with chloroform, and then washed with 10% NaOH (added up to pH 13). The mixture was washed with a saturated brine solution, the organic layer was dried over magnesium sulfate, and distilled off under reduced pressure. The resulting primary compound was purified by a silica gel column chromatography (eluent: 5% methanol/chloroform) to obtain the target compound in 25% yield (307 mg). (The reaction using ethylpiperazine instead of methylpiperazine was performed as the above method.)[212] 1H-NMR (400MHz, DMSO) delta 3.64-3.48(m, 4H), 2.41-2.36(m, 4H), 2.33-2.29 (m,2H) 2.31(s, 3H), 1.62(br m, 2H), 1.25(br s, 36H), O.88(t, 3H ,J=6.8Hz).

	With thionyl chloride; at 45℃; for 1.66667h;Heating / reflux; Neat (no solvent);	In a dry 2-necked, round bottomed flask, equipped with a magnetic stirrer and fixed with a separalory funnel, containing 7.88ml (108mmol) of thionyl chlo?de, and a water condenser, is placed 20.44g (Ommol) of docosanoic acid Addition of the thionyl chlo?de is completed with heating to about 45 "C over the course of about 30 minutes. When addition of the thionyl chloride is complete the mixture is heated and stirred for an additional 70 minutes. The water condenser is then replaced with a distillation side arm condenser and the crude mixture is distilled. The crude distillate in the receiving flask is then fractionally distilled to obtain the acyl chlo?de, docosanoyl chlo?de. This acyl chloride, 21.6Og (Ommol), is put into a dry separatory funnel and combined with 100ml of dry dichloromethane for use in the next step of the reaction.
	With thionyl chloride; In dichloromethane; for 4h;Heating;	Example 1; Preparation of 4-docosanoyl-1,1-dimethylpiperazin-1-ium iodide according to Reaction Scheme 1; 1. Preparation of 1-(4-methylpiperazine-1-yl)docosan-1-one; Thionyl chloride (0.43, 5.86 mmol) was added to a 0.1 M methylene chloride solution of docosanoic acid (1 g, 2.93 mmol) under stirring, and heated for 4 hours. The produced mixture was cooled to room temperature, and then methylpiperazine (1.30, 11.72 mmol) was added thereto at 0 C. under stirring for 2 hours. The produced mixture was diluted with chloroform, and then washed with 10% NaOH (added up to pH 13). The mixture was washed with a saturated brine solution, the organic layer was dried over magnesium sulfate, and distilled off under reduced pressure. The resulting primary compound was purified by a silica gel column chromatography (eluent: 5% methanol/chloroform) to obtain the target compound in 25% yield (307 mg). (The reaction using ethylpiperazine instead of methylpiperazine was performed as the above method.)1H-NMR (400 MHz, DMSO) delta 3.64-3.48 (m, 4H), 2.41-2.36 (m, 4H), 2.33-2.29 (m, 2H) 2.31 (s, 3H), 1.62 (br m, 2H), 1.25 (br s, 36H), 0.88 (t, 3H, J=6.8 Hz).
	With thionyl chloride; In dichloromethane; for 4h;Reflux; Inert atmosphere;	General procedure: Fatty acid 1 (2.9 mmol) was dissolved in anhydrous dichloromethane (0.1 M solution), and then thionyl chloride (3.0 equiv) was added under argon (Ar) atmosphere. The stirred suspension was heated to reflux for 4 h. Then the reaction mixture was cooled and poured onto crushed ice for 1 h. Piperazine (5.8 mmol) was added dropwise, and the reaction mixture was then allowed to warm up to room temperature and stirred for 2 h. NaOH solution (10%) was added (final pH 13), and the mixture was extracted with chloroform. The organic layer was washed with brine, dried over anhydrous MgSO4, and then concentrated in vacuo. The residue was purified by chromatography on silica gel with 5% MeOH/CHCl3 to afford the corresponding amides.
	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 0.333333h;	To a solution of docosanoic acid (2.7 g, 8.0 mmol) in dichloromethane (15 mL) was added N, N-dimethylformamide (5 drops) followed by oxalyl chloride (1.2 mL) . After stirring at room temperature for 20 minutes, the reaction mixture was concentrated and dissolved in tetrahydrofuran (5 mL) . A mixture of agmatine sulfate salt (2.7 g, 12 mmol), 2-propanol (15 mL) and water (20 mL) was added 27% aqueous sodium hydroxide to adjust pH 11. Then the above tetrahydrofuran solution was added to the solution of agmatine sulfate salt dropwise with adding 27% aqueous sodium hydroxide to keep pH=ll. The mixture was stirred at room temperature for 2 hours. The formed solid was filtered and dissolved in 30 mL of tetrahydrofuran . To the solution was added hydrogen chloride/tetrahydrofuran (1 mol/L, 5 30 mL) dropwise. After stirring for 30 minutes at room (1190) temperature, the mixture was concentrated to give N- docosanoylagmatine hydrochloride salt (SZ108, 2.94 g, yield 66%) as white solid. (1191) 1H-NMR (CD30D, 400 MHz): delta 3.31-3.30 (m, 2H) , 3.20 (t, 2H, (1192) 10 J=6.4 Hz), 2.29-2.25 (m, 1H) , 2.18-2.20 (m, 1H) , 1.61-1.58 (m, 4H), 1.2 (s, 40H) , 0.89 (t, 3H, J=6.4 Hz). (1193) MS: 453.3 [M+H]+
	With oxalyl dichloride; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; for 0.5h;	To a 72 dichloromethane solution (4.6 mL) of behenic acid (232 mg, 0.680 mmol) were added 73 oxalyl chloride (0.059 mL, 0.680 mmol), a catalytic amount of 21 DMF and 6 THF (1 mL). After stirring for 30 min, the mixture was concentrated under reduced pressure and the obtained residue was dissolved in THF (1 mL) to give a 252 behenoyl chloride solution. In a separate flask, a 2-propanol/aqueous solution (v/v=37/63) (5 mL) of compound (134 mg, 0.618 mmol) obtained in Example 242 27, step 2 was prepared. A 25% aqueous sodium hydroxide solution was added at 5 C. to adjust same to pH about 8-11 and a 252 behenoyl chloride/6 THF solution was added by 0.25 mL. After stirring at room temperature for 1 hr, the solid was collected by filtration, and washed with water to give crude crystals (225 mg). The crude crystals (136 mg) were suspended in 234 ethyl acetate (3.5 mL), 4N 13 hydrochloric acid/ethyl acetate (0.29 mL) was added under ice-cooling, and the mixture was stirred at room temperature for 30 min and concentrated. To the obtained residue was added 233 diethyl ether (5 mL) and the solid was collected by filtration to give a mixture (88.8 mg) of the object product and behenic acid. Thereto was added a saturated aqueous sodium hydrogen carbonate solution (5 mL) and the mixture was stirred for 1 hr, and the 254 solid was collected by filtration. To the obtained residue was added methanol, and the mixture was acidified with trifluoroacetic acid and insoluble material was filtered off. The filtrate was subjected to reversed-phase HPLC in the same manner as in Example 27, step 1 to give the title compound (30.6 mg, 0.0543 mmol). (1644) 1H-NMR (400 MHz, DMSO-d6) delta7.73 (t, J=5.6 Hz, 1H), 7.44 (t, J=5.6 Hz, 1H), 7.37-6.55 (m, 4H), 3.14-2.92 (m, 4H), 2.02 (t, J=7.4 Hz, 2H), 1.55-1.32 (m, 6H), 1.32-0.99 (m, 38H), 0.85 (t, 3H). (1645) MS(ESI)m/z: 468[M+H]+
	With thionyl chloride; In 1,2-dichloro-ethane; N,N-dimethyl-formamide; at 20℃;	Behenic acid (4.43 g, 13.0 mmol) was added to and dispersed in 1,2-dichloroethane (37 ml) and N, N-dimethylformamide (1000 mul, 13.0 mmol).Add thionyl chloride (4.7 ml, 65.0 mmol),It reacted at room temperature. After completion of the reaction, concentration under reduced pressure was carried out to obtain solid behenoyl chloride. This was used as it is in the next reaction.
	With thionyl chloride; In chloroform;	A series of three prodrugs was synthesized by esterification of the 10- hydroxyl group on CAB yielding lipophilic prodrugs with 14, 18 and 22 carbon linkers named MCAB, M2CAB, and M3 CAB. Initially, CAB was dried from anhydrous pyridine and then suspended in anhydrous DMF. The mixture was cooled to 0C under argon. DIE A (2 equivalents) was used to deprotonate the 10-hydroxyl group of CAB, which was further reacted with 2 equivalents myristoyl chloride or stearoyl chloride for 24 hours to obtain MCAB or M2CAB respectively. M3CAB synthesis was a two-step process. In the first step, behenyl chloride was synthesized by chlorination of the carboxylic acid group of behenic acid in anhydrous chloroform using 4 equivalents thionyl chloride. CAB dried from anhydrous pyridine and resuspended in anhydrous DMF in the presence of 4 equivalents trietheylamine was further added to the behenyl chloride in DMF at 0C under argon followed by heating the reaction at 50C for 24 hours. All the resultant prodrugs were purified by silica gel column chromatography using an initial mobile phase of 4: 1 ethyl acetate: hexanes for initial fractions, then 9: 1 ethyl acetate: hexanes for the remainder. Finally, the prodrugs were precipitated and washed in diethyl ether, dried under vacuum to obtain a white powder with average yield of 85-95%.

Reference： [1]Monatshefte fur Chemie,1913,vol. 34,p. 1132
[2]Journal of the American Chemical Society,1984,vol. 106,p. 7033 - 7037
[3]Journal of Physical Chemistry,1993,vol. 97,p. 12848 - 12857
[4]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,1993,vol. 227,p. 271 - 276
[5]Liebigs Annales,1995,p. 755 - 764
[6]Tetrahedron,2002,vol. 58,p. 369 - 375
[7]European Journal of Organic Chemistry,2004,p. 468 - 473
[8]Journal of Organic Chemistry,2007,vol. 72,p. 7757 - 7760
[9]Patent: US4643990,1987,A
[10]Patent: US7319157,2008,B1 .Location in patent: Page/Page column 9
[11]Patent: WO2008/18778,2008,A1 .Location in patent: Page/Page column 13
[12]Patent: WO2008/101310,2008,A1 .Location in patent: Page/Page column 9-10
[13]Patent: US2010/144708,2010,A1 .Location in patent: Page/Page column 7
[14]European Journal of Medicinal Chemistry,2011,vol. 46,p. 2861 - 2866
[15]Analytical Chemistry,2012,vol. 84,p. 2388 - 2394
[16]Synlett,2012,vol. 23,p. 2389 - 2392
[17]Patent: WO2017/73797,2017,A1 .Location in patent: Paragraph 0196
[18]Journal of Medicinal Chemistry,2018,vol. 61,p. 3224 - 3230
[19]Dalton Transactions,2018,vol. 47,p. 7135 - 7143
[20]Patent: US2018/311342,2018,A1 .Location in patent: Paragraph 1642-1645
[21]Chemical Communications,2019,vol. 55,p. 711 - 714
[22]Patent: JP2019/89719,2019,A .Location in patent: Paragraph 0029; 0042; 0054
[23]Patent: WO2020/86555,2020,A1 .Location in patent: Page/Page column 36; 39

8
[ 112-85-6 ]
[ 55726-23-3 ]

Reference： [1]Synthetic Communications,2004,vol. 34,p. 3349 - 3358
[2]Chemische Berichte,1931,vol. 64,p. 2511
[3]Life Sciences,1996,vol. 58,p. 1347 - 1357
[4]Journal fur praktische Chemie (Leipzig 1954),1990,vol. 332,p. 579 - 583

9
[ 6066-82-6 ]
[ 112-85-6 ]
[ 58047-86-2 ]

Yield	Reaction Conditions	Operation in experiment
73%	With dicyclohexyl-carbodiimide In chloroform
73%	With 4-dimethylaminopyridine; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride In dichloromethane	4 [00638] Compound 1 (Sigma-Aldrich 216941) (0.300 g) was dissolved in 4.5 mL of DCM. Then EDC (Oakwood Chemical 024810) (0.211 g) was added to the solution. Then NHS (Sigma-Aldrich 130672) (0.203 g) was added to the mixture. Finally DMAP (Sigma- Aldrich 107700) (0.0215 g) was added. The reaction was allowed to stir overnight. The solution was diluted with 40 mL of DCM, and washed with acidic H2O (3x7 mL), dried with Na2SO4, filtered and concentrated on rotary evaporator. The concentrated product was dry loaded (3 mL of silica) onto 12 G Redi-Sep Gold Rf column in (mobile phase A : mobile phase B) Hex : EtOAc 0->50% over 25 minutes. The fractions containing product were collected and concentrated on rotary evaporator. Yield 283 g (73%.)
73%	With 4-dimethylaminopyridine; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride In dichloromethane	Synthesis of C22-PEG5K-Mal Compound 1 (Sigma-Aldrich 216941) (0.300 g) was dissolved in 4.5 mL of DCM. Then EDC (Oakwood Chemical 024810) (0.211 g) was added to the solution. Then NHS (Sigma-Aldrich 130672) (0.203 g) was added to the solution. Finally, DMAP (Sigma- Aldrich 107700) (0.0215 g) was added. The reaction mixture was allowed to stir overnight. The solution was diluted with 40 mL of DCM, and washed with acidic H2O (3 x 7 mL), dried with Na2SO4, filtered and concentrated under vacuum. The concentrated product was dry loaded (3 mL of silica) onto 12 G Redi-Sep rf Gold column in (mobile phase A : mobile phase B) Hex : EtOAc 0->50% over 25 minutes. The fractions containing product 2 were collected and concentrated. Yield 283 g (73%.)

70%	With dicyclohexyl-carbodiimide In chloroform at 0 - 22℃; for 16h;
	With dicyclohexyl-carbodiimide In tetrahydrofuran; ethyl acetate Ambient temperature;

Reference： [1]Anzai; Lee; Osa [Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 9, p. 3018 - 3020]
[2]Current Patent Assignee: ARROWHEAD RESEARCH CORP - WO2022/56269, 2022, A1 Location in patent: Paragraph 00638
[3]Current Patent Assignee: ARROWHEAD RESEARCH CORP - WO2022/56277, 2022, A1 Location in patent: Paragraph 0377-0378
[4]Trinh, Tuan; Chidchob, Pongphak; Bazzi, Hassan S.; Sleiman, Hanadi F. [Chemical Communications, 2016, vol. 52, # 72, p. 10914 - 10917]
[5]Furuta, Rhyuji; Kawata, Shigeo; Naruto, Shunsuke; Minami, Akira; Kotani, Shozo [Agricultural and Biological Chemistry, 1986, vol. 50, # 10, p. 2561 - 2572]

10
[ 78-26-2 ]
[ 112-85-6 ]
Docosanoic acid 2-docosanoyloxymethyl-2-methyl-pentyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid Heating; Yield given;

Reference： [1]Bhatnagar, A. K.; Bhattacharyya, K. K. [Journal of the Indian Chemical Society, 1981, vol. 58, p. 594 - 596]

11
[ 818-88-2 ]
[ 112-85-6 ]
[ 629-83-4 ]

Yield	Reaction Conditions	Operation in experiment
48.6%	With sodium methylate In methanol at 35℃; electrolysis on Pt electrode, 0.05 amps, 50-60 volts;

Reference： [1]Joshi, U. R.; Kapadi, A. H. [Synthetic Communications, 1984, vol. 14, # 7, p. 681 - 686]

12
[ 929-77-1 ]
[ 112-85-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide

Reference： [1]Joshi, U. R.; Kapadi, A. H. [Synthetic Communications, 1984, vol. 14, # 7, p. 681 - 686]

13
[ 4740-78-7 ]
[ 112-85-6 ]
[ 277749-19-6 ]

Reference： [1]Synlett,2000,p. 248 - 250

15
2-acetyl-2-docosanoyl-tridecanedioic acid diethyl ester [ No CAS ]
[ 2389-02-8 ]
[ 112-85-6 ]
[ 122335-19-7 ]

Yield	Reaction Conditions	Operation in experiment
	Anschliessend mit verd. H₂SO₄ und Na₂CO_3.;

Reference： [1]Francis; King; Willis [Journal of the Chemical Society, 1937, p. 1001]

16
[ 112-85-6 ]
[ 29022-11-5 ]
[ 35661-39-3 ]
[ 109745-15-5 ]
Li D-Lac, Fmoc-D-ALa, Fmoc-Lys(Ac) [ No CAS ]
N-docosanoyl-Gly-Ala-D-γ-Glu-Lys(N-ε-acetyl)-D-Ala-D-lactate [ No CAS ]

Reference： [1]Tetrahedron Letters,1997,vol. 38,p. 5229 - 5232

17
[ 112-85-6 ]
[ 1599-68-4 ]

Reference： [1]Organometallics,2011,vol. 30,p. 1389 - 1394
[2]Chemical Communications,2012,vol. 48,p. 2552 - 2554
[3]Chemical Communications,2004,p. 724 - 725
[4]Russian Journal of Physical Chemistry,2001,vol. 75,p. 2069 - 2075

18
[ 112-85-6 ]
[ 661-19-8 ]

Yield	Reaction Conditions	Operation in experiment
87.6%	With sodium tetrahydroborate; iodine; In tetrahydrofuran; at 0 - 30℃;	Sodium borohydride (2.9 g) was suspended in THF (100 ml) at 20-30 C and cooled to 0-5 C. Thereafter, added a solution of iodine (7.5 g) dissolved in THF (30 ml) over a period of 1-2 h at 0-5 C followed by a solution of docosanoic acid (20 g) dissolved in THF (140 ml) in 30-40 min. The reaction mixture was stirred for 2-4 h at 20-30 C. After completion of reaction, the reaction mixture was carefully quenched with dil. HC1 (30 ml, 3N) at 20-30 C and evaporated the solvent under reduced pressure (40-50 mm Hg) at 40-45 C to get a turbid oily mass. To the above residue DM water (200 ml) was added and extracted the product in methyl-tert-butyl ether (300 ml). The organic extract was washed with an aqueous solution of 10% w/w sodium hydroxide (100 ml), an aqueous solution of 5% w/w sodium metabisulfite and finally with DM water (100 ml). Thereafter, the organic extract was concentrated under reduced pressure (20-40 mm Hg) at 40-50 C to get a white colour residue. The above residue was dissolved in n- heptane (100 ml) at 40-45 C and stirred for an hour at 20-25 C. The resulting solid was filtered and dried under reduced pressure (10-20 mm Hg) to afford 16.8 g of the title compound. Yield: 87.6 % of theory Chromatographic purity (by GC): >98 %
	With acetic acid;	Method: 4 g of docosanoic acid are dissolved in 150 ml of anhydrous ether. LeAlH4 is progressively introduced. On completion of the reaction, 150 ml of an aqueous solution of 1 N acetic acid are introduced. The ethereal phase is then separated off, decanted and dried. Rectification in vacuo gives approximately 1 g of 1-docosanol. Melting point: 69-71 C. Boiling point: 180 C. at 0.22 mm Hg Microanalysis found for C22 H46 O: C%=80.98 H%=14.11 O%=4.90. The alkanols of Examples 2 to 6 were obtained by reducing the corresponding acid or carbonyl derivative.

Reference： [1]Patent: WO2018/220504,2018,A1 .Location in patent: Page/Page column 8; 9
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1996,vol. 35,p. 1239 - 1241
[3]Patent: US4186211,1980,A

19
[ 72849-35-5 ]
[ 112-85-6 ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1956,vol. 76,p. 960
Chem.Abstr.,1957,p. 891

20
[ 112-85-6 ]
[ 56552-80-8 ]
3-O-benzyl-1,2-di-O-docosanoyl-Sn-glycerol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With dicyclohexyl-carbodiimide In pyridine at 20℃; for 22h;

Reference： [1]Current Patent Assignee: NISSIN FOODS HOLDINGS CO.,LTD. - US6337390, 2002, B1 Location in patent: Example 36

21
[ 8001-23-8 ]
[ 373-49-9 ]
[ 112-80-1 ]
[ 112-79-8 ]
[ 544-70-7 ]
[ 544-70-7 ]
[ 7307-45-1 ]
[ 1072-36-2 ]
[ 60-33-3 ]
[ 60-33-3 ]
[ 29204-02-2 ]
[ 506-30-9 ]
[ 112-85-6 ]
[ 544-63-8 ]
[ 57-10-3 ]
[ 57-11-4 ]
[ 117624-52-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; ethanol; water; at 150 - 215℃; under 7500.75 - 24002.4 Torr; for 0 - 6h;Product distribution / selectivity;	Example 1; A comparison was carried out between reactions carried out in 96% ethanol (according to the invention), and 99.9% ethanol (dry ethanol, comparative example). Both reactions were catalysed by sodium hydroxide, which was used in the form of dry pellets. Safflower oil was used as source for linoleic acid. The sample removed at t=0 hr is the first sample taken when the desired temperature was reached. The reaction mixture was analysed by the fatty acid methyl ester (FAME) method using gas chromatography. The results for the process using 96% ethanol are set out in the following table: The results for the process using 99.9% ethanol are set out in the following table When 96% ethanol was used with addition of extra water, 96.6% of C18:2c was converted in 6 hours. Using dry ethanol gave a conversion of 99.5% in 6 hours. However, the reaction mixture with the lower water content produced higher amounts of the conjugated trans, tans isomer, was very viscous and difficult to stir and to remove samples.; Example 4; COMPARATIVE EXAMPLE; A comparative example was carried out to show the formation of trans, trans isomers at temperatures outside the claimed range. Saffower oil (200 g), caustic soda (45 g) and 95-97% ethyl alcohol (450 ml) were heated under a pressure of 30-32 bar at 210-215 C. for 4 hours. Samples of the reaction mixture were taken at the start of the reaction and at 2 and 4 hours. The reaction mixture was analysed by the fatty acid methyl ester (FAME) method using gas chromatography. The results for the trans, trans conjugated isomer of CLA were as follows:; Example 1; A comparison was carried out between reactions carried out in 96% ethanol (according to the invention), and 99.9% ethanol (dry ethanol, comparative example). Both reactions were catalysed by sodium hydroxide, which was used in the form of dry pellets. Safflower oil was used as source for linoleic acid. The sample removed at t=0 hr is the first sample taken when the desired temperature was reached. The reaction mixture was analysed by the fatty acid methyl ester (FAME) method using gas chromatography. The results for the process using 96% ethanol are set out in the following table: The results for the process using 99.9% ethanol are set out in the following table When 96% ethanol was used with addition of extra water, 96.6% of C18:2c was converted in 6 hours. Using dry ethanol gave a conversion of 99.5% in 6 hours. However, the reaction mixture with the lower water content produced higher amounts of the conjugated trans, tans isomer, was very viscous and difficult to stir and to remove samples.
	With potassium hydroxide; ethanol; water; at 150℃; under 7500.75 - 9000.9 Torr; for 0 - 6h;Product distribution / selectivity;	Example 2; An experiment was carried out to compare processes carried out using ethanol (EtOH) (according to the invention) and propylene glycol (MPG) (comparative example). These reactions were catalysed by potassium hydroxide. Safflower oil was used as source for linoleic acid. The water in the system is from the potassium hydroxide used. Reaction Conditions: The results of FAME analysis of the reaction in ethanol were as follows: The results of FAME analysis of the reaction in propylene glycol were as follows: When 96% ethanol was used as solvent, 99.5% of C18:2c was converted in 2 hours. Using propylene glycol gave a conversion of 90.7% in 2 hours.; Example 3; A series of five experiments was carried out using safflower oil (300 g)>potassium hydroxide pellets and 96% ethanol (250 ml) as the solvent. The amount of potassium hydroxide was varied (72.6 g, 77.5 g, 85.3 g, 103 g and 120.6 g). Since the pellets used contain about 15% water, the water content also varied as a result of varying the amount of potassium hydroxide. The amount of water used in the examples was 10.9%, 11.3%, 11.9%, 13.3% and 14.6%. A measurement of the conversion of linoleic acid showed that the rate of reaction increased with increasing water content, at these levels of water content.
	With potassium hydroxide; water; In propylene glycol; at 150℃; under 7500.75 - 9000.9 Torr; for 0 - 6h;Product distribution / selectivity;	Example 2; An experiment was carried out to compare processes carried out using ethanol (EtOH) (according to the invention) and propylene glycol (MPG) (comparative example). These reactions were catalysed by potassium hydroxide. Safflower oil was used as source for linoleic acid. The water in the system is from the potassium hydroxide used. Reaction Conditions: The results of FAME analysis of the reaction in ethanol were as follows: The results of FAME analysis of the reaction in propylene glycol were as follows: When 96% ethanol was used as solvent, 99.5% of C18:2c was converted in 2 hours. Using propylene glycol gave a conversion of 90.7% in 2 hours.

Reference： [1]Patent: US2005/124818,2005,A1 .Location in patent: Page/Page column 4-5
[2]Patent: US2005/124818,2005,A1 .Location in patent: Page/Page column 4-5
[3]Patent: US2005/124818,2005,A1 .Location in patent: Page/Page column 4-5

22
[ 112-85-6 ]
silver nitrate [ No CAS ]
[ 2489-05-6 ]

Yield	Reaction Conditions	Operation in experiment
99%	In ammonium hydroxide; ethanol hot (50°C) soln. docosanoic acid in EtOH was added slowly to hot soln. AgNO3 in aq. NH4OH at 50°C in the dark; ppt. was washed with water, extracted with EtOH and dried in vacuo for 12 h;
	In water dipping Langmuir-Blodgett film of behenic acid on CaF2 substrate into soln. of AgNO3, 15 min; washing with H2O, drying in air;

Reference： [1]Kostas, Ioannis D.; Vallianatou, Kalliopi A.; Kyritsis, Panayotis; Zedník, Jiří; Vohlídal, Jiří [Inorganica Chimica Acta, 2004, vol. 357, # 10, p. 3084 - 3088]
[2]Leloup, J.; Maire, P.; Ruaudel-Teixier, A.; Barraud, A. [Journal de Chimie Physique et de Physico-Chimie Biologique, 1985, vol. 82, # 6, p. 695 - 700]

23
[ 112-85-6 ]
[ 629-94-7 ]

Yield	Reaction Conditions	Operation in experiment
	With 1% Pd/C Selcat Q6 In dodecane at 300℃; for 2.5h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Simakova, Irina; Simakova, Olga; Mäki-Arvela, Päivi; Murzin, Dmitry Yu. [Catalysis Today, 2010, vol. 150, # 1-2, p. 28 - 31]

24
[ 111-20-6 ]
[ 50-70-4 ]
[ 112-85-6 ]
poly(sorbitol sebacate) behenate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 240℃; for 5 - 6h;	Anhydrous polyol P2 (36.4 g: 0.2 mol), dicarboxylic acid DA2 (32.3 g; 0.16 mol), monocarboxylic fatty acid FA2 (136.1 g; 0.4 mol), catalyst Cat2 [H3PO3 (0.26 g; 1.59 mol% on polyol) and NaOH (0.64 g 50% aqueous solution; 4 mol% on polyol)] were charged to a 250ml round bottomed flask fitted with a propeller stirrer, side-arm water condenser and collection flask, nitrogen sparge thermometer (thermocouple) and isomantle. The mixture was heated under stirring (300 rpm) to 24O0C under nitrogen sparge removing water of reaction through the condenser. The reaction was monitored by acid value and stopped when the acid value was less than 10 (after 5 to 6 hrs) and the product discharged. The measured molecular weight was Mn 3670; Mw 14700 and MP 640C.
	potassium carbonate; at 170℃; under 75.0075 Torr; for 5h;	Synthesis Example SE2 - Poly(sorbitol sebacate) behenate Anhydrous P2 (32.76 g; 0.18 mol), DA2 (18.18 g; 0.09 mol), FA2 (91.80 g; 0.27 mol) and Cat1(1.86 g; 7.5 mol% based on polyol) were charged to a reaction vessel as described in SE1 and the mixture heated with stirring (300 rpm) to 17O0C under nitrogen sparge and at a vacuum of 100 mbar (gauge). The reaction was monitored by acid value and stopped when this fell below 20 (after 4 to 5 hrs) and the product discharged. The measured molecular weight was Mn 1480; Mw 3220
	potassium carbonate; at 170℃; under 75.0075 Torr; for 9.5h;	The products made in the Synthesis Examples and the reaction conditions used are summarised in Table 1 below. Amounts of polyol diacid and fatty acid are molar proportions (based on polyol = 1) and of catalyst are mole percent (based on polyol).

	sodium hydroxide; at 210℃; for 4.5h;	The products made in the Synthesis Examples and the reaction conditions used are summarised in Table 1 below. Amounts of polyol diacid and fatty acid are molar proportions (based on polyol = 1) and of catalyst are mole percent (based on polyol).
	at 240℃; for 4h;	The products made in the Synthesis Examples and the reaction conditions used are summarised in Table 1 below. Amounts of polyol diacid and fatty acid are molar proportions (based on polyol = 1) and of catalyst are mole percent (based on polyol).

Reference： [1]Patent: WO2007/74331,2007,A1 .Location in patent: Page/Page column 11
[2]Patent: WO2007/74331,2007,A1 .Location in patent: Page/Page column 11-12
[3]Patent: WO2007/74331,2007,A1 .Location in patent: Page/Page column 11-12
[4]Patent: WO2007/74331,2007,A1 .Location in patent: Page/Page column 11-12
[5]Patent: WO2007/74331,2007,A1 .Location in patent: Page/Page column 11-12

25
[ 111-20-6 ]
[ 112-85-6 ]
[ 56-81-5 ]
poly(glycerol sebacate) behenate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 220℃; for 4 - 5h;	P1 (100.0 g; 1.09 mol), DA2 (175.6.2 g; 0.87 mol), FA2 (369.6 g; 1.09 mol) and Cat 3 (0.89 g; 1 mo.% on polyol) were charged to a 1 I round bottomed flask fitted as described in SE1 and the mixture heated with stirring (300 rpm) to 22O0C under nitrogen sparge. The reaction was stopped when the acid value fell below 5 (after 4 to 5 hrs) and the product discharged.
	toluene-4-sulfonic acid; at 170℃; under 75.0075 Torr; for 3.5h;	The products made in the Synthesis Examples and the reaction conditions used are summarised in Table 1 below. Amounts of polyol diacid and fatty acid are molar proportions (based on polyol = 1) and of catalyst are mole percent (based on polyol).
	phosphorous acid; at 220℃; for 4h;	The products made in the Synthesis Examples and the reaction conditions used are summarised in Table 1 below. Amounts of polyol diacid and fatty acid are molar proportions (based on polyol = 1) and of catalyst are mole percent (based on polyol).

	phosphorous acid; at 220℃; under 75.0075 Torr; for 6.5h;	The products made in the Synthesis Examples and the reaction conditions used are summarised in Table 1 below. Amounts of polyol diacid and fatty acid are molar proportions (based on polyol = 1) and of catalyst are mole percent (based on polyol).
	at 240℃; for 4.5h;	The products made in the Synthesis Examples and the reaction conditions used are summarised in Table 1 below. Amounts of polyol diacid and fatty acid are molar proportions (based on polyol = 1) and of catalyst are mole percent (based on polyol).

Reference： [1]Patent: WO2007/74331,2007,A1 .Location in patent: Page/Page column 11-12
[2]Patent: WO2007/74331,2007,A1 .Location in patent: Page/Page column 11-12
[3]Patent: WO2007/74331,2007,A1 .Location in patent: Page/Page column 11-12
[4]Patent: WO2007/74331,2007,A1 .Location in patent: Page/Page column 11-12
[5]Patent: WO2007/74331,2007,A1 .Location in patent: Page/Page column 11-12

26
(L)-2-hydroxy-1-hexadecyloxycarbonylethylammonium chloride [ No CAS ]
[ 112-85-6 ]
N-docosanoyl-(L)-serine hexadecyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%		N-Docosanoyl-(L)-serine hexadecyl ester(L)-2-Hydroxy-l-hexadecyloxycarbonylethylammonium chloride (290 mg, 0.8 mmol) and 4-dimethylaminopyridine (107 mg, 0.88 mmol) were stirred in 10 ml of dry chloroform. Separately, docosanoic acid (270 mg, 0.8 mmol) and dicyclohexyl carbodiimide (165 mg, 0.8 mmol) were mixed in dry chloroform and the solution was added to the reaction. The reaction mixture was stirred at lab temperature for 20 hours and then concentrated under reduced pressure. The crude product was suspended in hexane and crystals were filtered out after 1 hour. Dicyclohexylurea was removed by suspending crystals in methanol and filtering them out after 1 hour. The pure product was obtained via chromatography on silica gel using the mobile phase chloroform/ethyl acetate 8:2. Yield: 458 mg (92 %); colorless crystals; melting point = 83 - 86 C; 6.3 (0.8; CHCl3); IR (KBr): vmax 3428, 2919, 2850, 1734, 1647, 1541, 1468, 1235, 720 cm'1; 1H NMR (300 MHz, CDCl3): delta 6.41 (IH; d; J = 6.9 Hz; NH); 4.70 - 4.60 (IH; m; CHN); 4.17 (2H; t; J= 6.7 Hz; OCH2); 3.95 (2H; dd; J1 = 6.1 Hz; J2 = 3.9 Hz; CH2OH); 2.62 (IH; t; J= 5.9 Hz; OH); 2.26 (2H; t; J= 7.6 Hz; COCH2); 1.75 - 1.50 (4H; m; 2CH2); 1.50 - 1.05 (62H; m; 31 CH2); 0.87 (6H; t; J= 6.7 Hz; 2CH3); 13C NMR (75 MHz, CDCl3): delta 173.8; 170.5; 66.2; 64.0; 54.9; 36.5; 31.9; 29.7; 29.7; 29.6; 29.5; 29.4; 29.2; 29.2; 28.5; 25.8; 25.6; 22.7; 14.1.

Reference： [1]Patent: WO2007/147370,2007,A2 .Location in patent: Page/Page column 8

27
[ 112-85-6 ]
C₅₁H₈₈N₂O₁₁ [ No CAS ]
[ 1314766-61-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 0 - 15℃;Inert atmosphere;	A solution of compound 11 (250 mg, 0.248 mmol) and 50% TFA in CH2Cl2 (10 mL) was stirred for 3 h. When TLC showed complete conversion of the starting material, the solution was diluted with dichloromethane (25 mL) and washed successively with ice-cold NaHCO3 (2×50 mL) and brine (50 mL). Then, the organic layer was separated, dried over MgSO4, and evaporated under vacuum. The crude amine produced was used for the next step without any further purification.To a solution of the crude amine and docosanoic acid (170 mg, 0.248 mmol) in dry DMF (10 mL) was added EDC (55 muL, 0.298 mmol) at 0 C under a nitrogen atmosphere. After 30 min, the reaction mixture was warmed to 15 C and stirred overnight. The solvents were evaporated and the residue was dissolved in dichloromethane (30 mL) and washed with brine (25 mL). The organic layer was dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by flash chromatography using n-hexane/EtOAc (2:1) to afford pure 12a (250 mg, 82%) as a colorless oil. [alpha]D20 +5.8 (c 1.3, CHCl3). 1H NMR (CDCl3, 400 MHz): delta 7.5 (d, 1H, J=8.5 Hz, NH), 7.35 (m, 5H, C6H5), 5.40 (d, 1H, J=3.2 Hz, H-4), 5.20 (dd, 1H, J=7.7, 10.5 Hz, H-2), 5.12 (dd, 1H, J=3.2, 10.5 Hz, H-3), 4.7 (d, 1H, J=11.6 Hz, CH2C6H5), 4.57 (d, 1H, J=7.5 Hz, H-1), 4.5 (m, 2H, CH2C6H5, H'-2), 4.4 (m, 1H, H-5), 4.06 (m, 4H), 3.7 (m, 1H), 3.58 (dd, 1H, J=6.1, 9.4 Hz), 2.81, 2.79 (2dd, 2H, J=3.91, 12.5 Hz), 2.56 (m, 2H), 2.12 (t, 3H, COCH2), 1.59 (m, 2H), 1.45 (m, 4H), 1.26 (m, 75H), 1.17, 1.16, 1.12 (3s, 27H, 3× (CO)OC(CH3)3), 0.89 (t, 6H, 2× CH3). 13C NMR (400 MHz, CDCl3): delta 177.7 (2), 177.1, 176.7 (2), (4× COC(CH3)3), 173.3 (COCH2CH2), 138.2, 128.4 (2), 127.9 (2), 127.7 (C6H5) 101.4 (C-1), 77.2, 75.7, 72.0, 71.1, 70.8, 69.1, 68.6, 66.6, 61.0, 50.7, 39.0, 38.8, 38.7 (2), 31.9, 29.7 (5), 29.6, 29.3, 28.3 (3), 27.1 (12), 22.6, 14.0. Elemental analysis: calcd for C73H130N2O12 (1227.81): C 71.41, H 10.67, N 2.28; found C 71.21, H 10.60, N 2.20.

Reference： [1]Tetrahedron,2011,vol. 67,p. 5176 - 5183

28
[ 86227-47-6 ]
[ 112-85-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen In methanol at 20℃; for 3h;

Reference： [1]Location in patent: experimental part Pandarus, Valerica; Gingras, Genevieve; Beland, Francois; Ciriminna, Rosaria; Pagliaro, Mario [Organic Process Research and Development, 2012, vol. 16, # 7, p. 1307 - 1311]

29
[ 17364-00-0 ]
[ 112-85-6 ]
[ 152914-56-2 ]

Yield	Reaction Conditions	Operation in experiment
56%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; at 0℃; for 4h;	General procedure: EDCI (383 mg, 2.0 mmol), DMAP (19 mg, 0.16 mmol), and 1 (204 mg, 0.88 mmol) were added to a solution of lauric acid (160 mg, 0.80 mmol) in a 1:1 mixture of anhydrous THF/CH2Cl2 (10 mL) at 0 C. The reaction mixture was allowed to stir for 4 h. The reaction mixture was then diluted with CH2Cl2 (15 mL) and H2O (15 mL). The organic layer was separated, dried over MgSO4, and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel (0-15% ethyl acetate/hexanes) to yield 2a (221 mg, 67%) as a colorless oil.

Reference： [1]Tetrahedron,2012,vol. 68,p. 5422 - 5428

30
[ 125162-81-4 ]
[ 112-85-6 ]
[ 1353218-55-9 ]

Yield	Reaction Conditions	Operation in experiment
88%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In acetonitrile; at 50℃; for 10h;	Behenic acid (4) (170 g, 0.50 mol) was dissolved in 0.80L acetonitrile with magnetic stirring. 2-(4-aminobutyl)propane-1,3-diol (3) (147 g, 1.0 mol) and 1-ethyl-3-(3-dimethyl-aminopropyl)carbodiimide hydrochloride (115g, 0.60 mol) were added. The mixture was allowedto react 10 hrs. at 50C. The solvent was evaporated, then petroleum ether (1.0L) and water (0.50 L) were added and stirring was continued for an additional 20min. The organic phase was washed with water (5×0.30 L) and dried over anhydrous sodium sulfate. Thesolvent was removed by evaporation to give 206 g (88%) of a white powder. 1HNMR (CDCl3): delta= 0.88 (t, 3H), 1.25-1.62 (m, 44H), 2.16(t, 2H), 3.28(m, 2H), 3.68 (dd 2H), 3.79 (dd, 2H), 5.50 (s, 1H) ppm; MS (ESI): Calcd. for C29H59NO3: 469.5,Found: 470.7 [M+H]+.

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 94 - 97

31
[ 18202-10-3 ]
[ 112-85-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 604 - 608

32
[ 112-85-6 ]
[ 127-06-0 ]
[ 1544620-10-1 ]

Yield	Reaction Conditions	Operation in experiment
64%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃;	General procedure: To a solution of eicosanoic acid (710mg, 2.27mmol), DMAP (20mg, 0.16mmol) and EDAC (463mg, 2.42mmol) in dried dichloromethane (10ml), acetone oxime (193mg, 2.64mmol) was added and the resulting solution was stirred overnight at rt. The reaction solution was passed through a short silica gel column with ethyl acetate/petroleum ether (60:40) as an eluent, affording the product as white crystalline material after evaporation of the solvents and recrystallization from petroleum ether (826mg, 2.25mmol) in 99% yield.

Reference： [1]Tetrahedron Asymmetry,2014,vol. 25,p. 125 - 132

33
[ 112-85-6 ]
[ 4136-95-2 ]
[ 1620745-13-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 25℃; for 0.5h;	General procedure: Hyaluronic acid (5 g, 12.5 mmol) was dissolved overnight in 100 ml of distilled water. To that solution 50 ml of THF were slowly added. After the solution was homogeneous, triethylamine (3.5 ml, 25 mmol) and DMAP (0.015 g, 0.125 mmol) were added and the mixture was stirred until a clear solution was obtained. At the same time and in a second reaction flask, the fatty acid was activated using the molar ratio described in Tables 1 and 2. The molar equivalents of the fatty acid as resumed in Tables 1 and 2 were dissolved in tetrahydrofurane (10 ml). After that, TEA (5 ml, 25 mmol) were added, followed by one molar equivalent of 2,4,6-trichlorobenzoyl chloride (TCBC). The formation of the aliphatic aromatic anhydride was carried out for 30 min at room temperature (25C). Then, the solution containing the mixed anhydride was added to the solution containing the polysaccharide. The mixture is allowed to react for 3 h at room temperature under vigorous stirring to ensure a good homogenization of the components. The crude product was isolated by precipitation with the addition of 100 ml of distilled water and a super-saturated solution of sodium chloride. After that the product was washed with an excess of anhydrous isopropanol (250 ml). The product was washed again with solutions of isopropanol: water (85%, v/v, 4× 250 ml). Finally, the precipitate was washed two more times with absolute isopropanol. The white precipitate was decanted and dried in an oven at 40C for at least 24 h. Yields of the reaction are resumed in Tables 1 and 2.

Reference： [1]Carbohydrate Polymers,2014,vol. 111,p. 883 - 891

34
[ 6066-82-6 ]
[ 112-85-6 ]
[ 114932-60-4 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1-hydroxy-pyrrolidine-2,5-dione; n-docosanoic acid In N,N-dimethyl-formamide for 0.0833333h; Stage #2: With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; Inert atmosphere;

Reference： [1]Liu, Kai; Zheng, Lifei; Liu, Qing; De Vries, Jan Willem; Gerasimov, Jennifer Y.; Herrmann, Andreas [Journal of the American Chemical Society, 2014, vol. 136, # 40, p. 14255 - 14262]

35
[ 7643-75-6 ]
[ 112-85-6 ]
1-O-docosanoylarabitol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%	With Novozym 435 (obtained from NovozymesA/S, Bagsvaerd, Denmark) In <i>tert</i>-butyl alcohol at 60℃; for 24h; Molecular sieve; Enzymatic reaction;

Reference： [1]Wei, Wei; Feng, Fengqin; Perez, Bianca; Dong, Mingdong; Guo, Zheng [Green Chemistry, 2015, vol. 17, # 6, p. 3475 - 3489]

36
[ 112-85-6 ]
[ 1622988-51-5 ]
C₄₀H₇₄O₄Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide; at 20 - 50℃;Inert atmosphere;	<strong>[112-85-6]Docosanoic acid</strong> (136.6 mg, 0.40 mmol) and the mono-TIPS-mono-isopropyl- phloroglucinol 11 b (100 mg, 0.30 mmol) were dissolved in dry CH2CI2 (6 mL) and dry DMF (1 .5 mL). DCC (82.7, 0.40 mmol) and DMAP (5 mg, 0.04 mmol) were added to the solution and the reaction was stirred at room temperature for 5h under nitrogen, and then overnight at 50C. Then, the mixture was left 2h at 4C to induce dicyclohexylurea crystallization. The urea residue was then filtered off, and the filtrate was washed with water and brine. The organic layer was dried on MgS04 and concentrated under reduced pressure. Purification of the crude material was performed by chromatography on silica gel (hexane/AcOEt 99.5/0.5) to afford (95 mg, 48%) the protected derivative as an uncolored oil. (0387) Deprotection of this protected-docosanoic-phloroglucinol (90 mg, 0.14 mmol) was performed using the general procedure used in example 1 and afforded 3- hydroxy-5-isopropoxyphenyl docosanoate (56 mg, 82%) as white solid after purification on silica gel chromatography (hexane/AcOEt 9/1). (0388) R, (hexane/AcOEt 9.5/0.5) 0.3; 1H NMR (500 MHz, CDCI3) delta 6.22 (t, J= 2.2 Hz, 1H), 6.17 (t, J= 2.1 Hz, 1H), 6.14 (t, J= 2.1 Hz, 1H), 6.07 (br, 1H), 4.44 (hept, J = 6.1 Hz, 1 H), 2.52 (t, J= 7.6 Hz, 2H), 1.75-1.69 (m, 2H), 1.42-1.34 (m, 4H), 1.30 (d, J= 6.1 Hz, 6H), 1.28- 1.22 (m, 30H), 0.88 (t, J= 7.0 Hz, 3H); 13C NMR (126 MHz, CDCI3) delta 173.1, 159.8, 157.7, 152.4, 102.0, 101.9, 101.26, 70.6, 34.8, 32.3, 30.0, 30.0, 29.7, 29.8, 29.7, 29.6, 29.4, 25.2, 23.0, 22.3, 14.5.

Reference： [1]Patent: WO2015/162265,2015,A1 .Location in patent: Page/Page column 58; 59

37
[ 112-85-6 ]
L-cystine dimethyl ester hydrochloride [ No CAS ]
Ν,Ν'-bis(docosanoyl)-L-cystine dimethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 20.5h;Cooling with ice;	To L-cystine dimethyl ester hydrochloride (250 mg, 0.73 mmol) were added N, N-dimethylformamide (5 mL) and behenic acid (597 mg, 1.75 mmol) at room temperature, and the mixture was cooled in an ice bath. To the obtained mixture were added 1- ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (336 . mg, 1.75 mmol), 1-hydroxybenzotriazole (237 mg, 1.75 mmol) and triethylamine (0.41 ml, 2.92 mmol), and the mixture was removed from the ice bath and stirred at room temperature for 20.5 hr. To the reaction mixture was added ethyl acetate (50 ml) and the mixture was filtered, and the filtered solid was slurry-washed with ethyl acetate/hexane (1/1, 50 ml) . After that, the obtained solid was dissolved in ethyl acetate (100 ml), washed with 10% aqueous citric acid solution (50 ml) and water, and the organic layer was concentrated. The obtained solid was slurry-washed again with ethyl acetate/hexane (3/2, 40 ml) to give N, ' -bis (docosanoyl) -L-cystine dimethyl ester (307 mg, 0.34 mmol, yield 46%) as a white solid. 1H-NMR(400 MHz, CDC13)5: 0.88 (t, 3H, J=6.8 Hz), 1.25 (m, 36H) , 1.62(m, 2H), 2.25(t, 2H, J=7.6 Hz), 3.18(dd, 1H, J=5.2 Hz, 14.4 Hz), 3.23(dd, 1H, J=5.2 Hz, 14.2 Hz), 3.77(s, 3H) , 4.87 (dt, 1H, J=5.2 Hz, 7.5 Hz), 6.40(d, 1H, J=7.2 Hz). ESIMS(m/z): 913.7 ( [M+H] +) .

Reference： [1]Patent: WO2015/163488,2015,A1 .Location in patent: Paragraph 0127

38
[ 16896-03-0 ]
[ 112-85-6 ]
methyl 2,3-di-O-benzyl-5-O-behenoyl-α-D-Araf [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃; for 0.5h;Inert atmosphere;	(a) A solution of N,N'-dicyclohexylcarbodi-imide (0.089g, 0.432mmol) in dry CH2Cl2 (1mL) was added dropwise to a stirred solution of 4 (0.10g, 0.29mmol), DMAP (0.042g, 0.343mmol) and behenic acid (0.10g, 0.29mmol) in dry CH2Cl2 (1mL) at 0C under nitrogen. The mixture was stirred for 30min then the precipitate of dicyclohexyl urea was filtered off and washed with CH2Cl2 (10mL), the solvent was evaporated and the residue was purified by column chromatography eluting with hexane/ethyl acetate (10:1) to afford methyl 2,3-di-O-benzyl-5-O-behenoyl-alpha-d-Araf as a colourless oil 7a (0.15g, 80%) [MALDI-Found (M+Na)+: 689.5, C42H66NaO6 requires: 689.4], [alpha]D24 +40 (c 0.10, CHCl3), which showed deltaH (500MHz, CDCl3): 7.41-7.28 (10H, m), 4.95 (1H, s), 4.59 (1H, d, J 12.0Hz), 4.57 (1H, d, J 12Hz), 4.52 (1H, d, J 12Hz), 4.49 (1H, d, J 12Hz), 4.29 (1H, dd, J 11.3, 2.8Hz), 4.24-4.15 (2H, m), 4.01 (1H, dd, J 2.9, 1.1Hz), 3.84 (1H, dd, J 6.3, 2.9Hz), 3.40 (3H, s), 2.33-2.26 (2H, m), 1.64-1.52 (2H, m), 1.34-1.18 (36H, m), 0.89 (3H, t, J 6.9Hz); deltaC (101MHz, CDCl3): 173.6, 137.5, 137.4, 128.45, 128.43, 127.9, 127.8, 107.3, 88.0, 83.4, 79.4, 72.3, 72.0, 63.5, 55.0, 34.1, 31.9, 29.7, 29.6, 29.62, 29.5, 29.3, 29.27, 29.1, 24.8, 22.7, 14.1; numax: 3034, 2915, 2849, 1741, 1471, 1100, 758cm-1.

Reference： [1]Tetrahedron,2016,vol. 72,p. 2849 - 2857

39
[ 112-85-6 ]
[ 129453-61-8 ]
C₅₄H₈₉F₅O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h;	3 Example 3 Synthesis and Structure Confirmation of Compound III 3 g (4.95 mmol) fulvestrant was added into a 250 mL round-bottom flask and then dissolved with 160 mL methylene chloride while stirring. Then, 0.0822 g (0.66 mmol) DMAP, 1.87 g (5.05 mmol) docosanoic acid and 1.02 g (4.98 mmol) DCC was added sequentially into said flask. After reacting under stirring at room temperature (e.g., 20±5° C.) for 48 h, the reaction was stopped. (0055) Reaction liquid was treated according to the post process in Example 2 to give 1.016 g white solid powder (purity 92.634%, determined by HPLC) (C18 column, mobile phase: 75% THF in water, flow rate: 1.0 mL/min, detection wavelength: 220 nm), which was Compound III, and the molar yield was 22.1%. (0056) IR (cm-1): 3607, 3424, 2919, 2851, 1754, 1495, 1471, 1199, 1153, 1141, 1112, 1081, 985, 719. (0057) 1HNMR (500 MHz, CDCl3, ppm): δ 7.28 (d, 1H), 6.83 (d, 1H), 6.77 (d, 1H), 3.74 (t, 1H, J=8 Hz), 2.91-1.05 (t, 79H), 0.89 (t, 3H), 0.77 (s, 3H). (0058) 13CNMR (125 MHz, CDCl3, ppm): δ 172.64, 148.53, 137.13, 126.91, 122.37, 118.64, 81.93, 52.83, 51.11, 46.48, 43.34, 41.68, 38.24, 36.89, 34.50, 33.15, 31.94, 30.56, 29.94, 29.86, 29.71, 29.67, 29.63, 29.62, 29.51, 29.48, 29.37, 29.35, 29.27, 29.17, 29.13, 28.81, 28.23, 27.12, 25.70, 25.01, 24.88, 23.16, 22.66, 14.50, 14.01, 11.50.

Reference： [1]Current Patent Assignee: XIAN LIBANG MEDICAL ENTERPRISE UNION CO LTD - US2016/60288, 2016, A1 Location in patent: Paragraph 0054-0058

40
[ 111-62-6 ]
[ 112-85-6 ]
C₄₂H₈₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With toluene-4-sulfonic acid; calcium chloride; at 85℃; under 15.0015 Torr; for 36h;	To a 250 mL three-necked round bottom flask was added 50 g (161 mmol, 1 eq) of ethyl oleate, 65.8 g (193 mmol, 1.2 eq) behenic acid, 22.2 g (129 mmol, 0.8 eq) of anhydrous p-toluenesulfonic acid,8 g of anhydrous calcium chloride, reacted at 85 C under vacuum (20 mbar) for 36 h, cooled to room temperature, 200 g of water was added, 500 mL of n-hexane, and the mixture was repeated twice.The resulting mixture was purified by chromatography to give 78.6 g (75% yield of white solid) behenic acid-9 (10) -hydroxy-stearate.

Reference： [1]Patent: CN106542995,2017,A .Location in patent: Paragraph 0090

41
[ 112-85-6 ]
[ 616-38-6 ]
[ 929-77-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	With triethylamine; at 160℃; for 5h;Autoclave; Green chemistry;	General procedure: Into a stainless steel pressure microreactor of capacity 17 mL was charged 5 wt % of zeolite NaY-Bf, 100 mmol of carboxylic acid, and 300-400 mmol of dimethyl carbonate, the reactor was hermetically closed, and the reaction mixture was heated at 180-200C for 5 h. On completion of the reaction the reactor was cooled to room temperature, opened, the reaction mixture was filtered through a bed of Al2O3. Unreacted dimethyl carbonate was distilled off, the residue was distilled at atmospheric pressure or in a vacuum, or it was crystallized from ethanol.
	With diiron nonacarbonyl; at 180℃; for 1h;Sealed tube;	General procedure: 1-3 mmol of catalyst Mn 2 (CO) 10 , 100 mmol of the carboxylic acid, and 300-400 mmol of dimethyl carbonate were placed into a 17 mL stainless steel microreactor. The reactor was sealed, and the reaction mixture was heated at 180 for 1 h. After the reaction was complete, the reactor was cooled to room temperature and opened. The reaction mixture was filtered through a layer of Al 2 O 3 . Unreacted dimethyl carbonate was distilled off, the residue was distilled at atmospheric or reduced pressure, or crystallized.

Reference： [1]Russian Journal of Organic Chemistry,2017,vol. 53,p. 163 - 168
Zh. Org. Khim.,2017,vol. 53,p. 177 - 181,5
[2]Russian Journal of General Chemistry,2018,vol. 88,p. 15 - 19
Zh. Obshch. Khim.,2018,vol. 88,p. 18 - 22,5

42
[ 112-85-6 ]
[ 5680-79-5 ]
N-docosanoyl glycine methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 19.5h;Cooling with ice;	To glycine methyl ester hydrochloride (500 mg, 3.98 mmol) were added N, -dimethylformamide (39.8 ml) and behenic acid (2.03 g, 5.97 mmol) at room temperature, and the mixture was cooled in an ice bath. Then, l-ethyl-3- (3- dimethylaminopropyl) carbodiimide hydrochloride (1.14 g, 5.97 mmol), 1-hydroxybenzotriazole (807 mg, 5.97 mmol), and (0972) triethylamine (1.67 ml, 12.0 mmol) were added, and the mixture was removed from the ice bath and stirred at room temperature for 19.5 hr. Thereafter, to the reaction mixture were added 10% aqueous citric acid solution (25 ml) and ethyl acetate (70 ml) and the mixture was filtered. The solid collected by filtration was slurry washed with hexane/ethyl acetate (2/3, v/v) (30 ml), diethyl ether (30 ml), and water (30 ml). Of the obtained solid (1.31 g) , 643 mg was taken and purified by silica gel column chromatography (hexane/ethyl acetate) to give N-docosanoyl glycine methyl ester (308 mg, 0.75 mmol, yield 38%) as a white solid. (0973) XH-NMR (400 MHz, CDC13)5: 0.88 (t, 3H, J=7.0 Hz), 1.25-1.30 (m, 36H) , 1.64(m, 2H) , 2.24(t, 2H, J=7.6 Hz), 3.77(s, 3H) , 4.05(d, 2H, J=5.2 Hz) , 5.91 (s, 1H) . (0974) ESlMS(m/z): 412.4 ( [M+H] +) , 823.8 ( [2 M+H] *) .

Reference： [1]Patent: WO2017/73797,2017,A1 .Location in patent: Paragraph 0164

43
[ 112-85-6 ]
[ 7524-50-7 ]
N-docosanoyl-L-phenylalanine methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 20h;Cooling with ice;	To L-phenylalanine methyl ester hydrochloride (500 mg, 2.32 mmol) were added N,N-dimethylformamide (23 ml), and behenic acid (1.18 g, 3.48 mmol) at room temperature, and the mixture was cooled in an ice bath. Then, l-ethyl-3- (3- dimethylaminopropyl) carbodiimide hydrochloride (667 mg, 3.48 mmol), 1-hydroxybenzotriazole (470 mg, 3.48 mmol), and (0985) triethylamine (0.97 ml, 6.95 mmol) were added, and the mixture was removed from the ice bath and stirred at room temperature for 20 hr. Thereafter, 10% aqueous citric acid solution (30 ml) and ethyl acetate (70 ml) were added and the mixture was filtered. The solid collected by filtration was purified by silica gel column chromatography (hexane/ethyl acetate) to give N-docosanoyl-L-phenylalanine methyl ester (300 mg, 0.60 mmol, yield 26%) as a white solid. (0986) 1H-NMR (400 MHz, CDC13)5: 0.88 (t, 3H, J=6.8 Hz), 1.20-1.32 (m, (0987) 36H) , 1.58 (m, 2H) , 2.16(t, 2H, J=7.2 Hz), 3.10(dd, 1H, J=8.4 Hz, 14.0 Hz), 3.16(dd, 1H, J=6.0 Hz, 14.0 Hz), 3.73(s, 3H) , 4.91(dt, 1H, J=7.6 Hz, 6.0 Hz), 5.83(d, 1H, J=7.6 Hz), 7.08-7.10 (m, 2H) , 7.22-7.31 (m, 3H) . (0988) ESIMS(m/z): 502.5 ( [M+H] +) .

Reference： [1]Patent: WO2017/73797,2017,A1 .Location in patent: Paragraph 0166

44
[ 112-85-6 ]
[ 6234-01-1 ]
N-docosanoyl-L-glutamic acid 5-tert-butyl-1-methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 22h;Cooling with ice;	To L-glutamic acid 5-tert-butyl-l-methyl ester (0992) hydrochloride (543 mg, 2.14 mmol) were added N,N- dimethylformamide (14.3 ml), and behenic acid (875 mg, 2.57 mmol) at room temperature, and the mixture was cooled in an ice bath. Then, l-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (493 mg, 2.57 mmol), 1-hydroxybenzotriazole (347 mg, 2.57 mmol), and triethylamine (0.60 ml, 4.3 mmol) were added, and the mixture was removed from the ice bath and stirred at room temperature for 22 hr. Ethyl acetate (25 ml) was added and the mixture was filtered. The solid collected by filtration was washed three times with ethyl acetate (10 ml) and three times with methanol (10 ml) to give N-docosanoyl-L- glutamic acid 5-tert-butyl-l-methyl ester (281 mg, 0.52 mmol, yield 24%) as a white solid. (0993) 1H-NMR (400 MHz, CDC13)5: 0.88 (t, 3H, J=7.0 Hz), 1.25-1.28 (m, 36H) , 1.44(s, 9H), 1.62(m, 2H) , 1.96(m, 1H) , 2.12(m, 1H) , (0994) 2.20(t, 2H, J=7.6 Hz), 2.30(m, 2H) , 3.74(s, 3H) , 4.59 (dt, 1H, J=5.2 Hz, 8.0 Hz), 6.19(d, 1H, J=7.6 Hz). (0995) ESIMS(m/z): 540.5 ( [M+H] +) , 1079.9 ( [2 M+H] +) .

Reference： [1]Patent: WO2017/73797,2017,A1 .Location in patent: Paragraph 0167

45
[ 112-85-6 ]
[ 6234-01-1 ]
N-docosanoyl-L-glutamic acid 1-methyl ester [ No CAS ]

Reference： [1]Patent: WO2017/73797,2017,A1

46
[ 112-85-6 ]
[ 2389-48-2 ]
N<SUP>6</SUP>-(tert-butoxycarbonyl)-N<SUP>2</SUP>-docosanoyl-L-lysine methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
13%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 22h; Cooling with ice;	10-1 [Synthetic Example 10-1] (1004) Synthesis of N⁶- (tert-butoxycarbonyl) -N²-docosanoyl-L-lysine methyl ester To N6- (tert-butoxycarbonyl) -L-lysine methyl ester (1006) hydrochloride (300 mg, 1.0 mmol) were added N,N- dimethylformamide (6.7 ml) and behenic acid (412 mg, 1.2 mmol) at room temperature, and the mixture was cooled in an ice bath. Then, l-ethyl-3- (3-dimethylaminopropyl) carbodiimide (1007) hydrochloride (232 mg, 1.2 mmol), 1-hydroxybenzotriazole (164 mg, 1.2 mmol), and triethylamine (0.28 ml, 2.0 mmol) were added, and the mixture was removed from the ice bath and stirred at room temperature for 22 hr. Thereafter, ethyl acetate (10 ml) was added and the mixture was filtered. The solid collected by filtration was washed three times with ethyl acetate (10 ml) to give N6- (tert-butoxycarbonyl) -N2-docosanoyl-L-lysine methyl ester (75.8 mg, 0.13 mmol, yield 13%) as a white solid. (1008) H-NMR (400 MHz, CDC13)5: 0.88(t, 3H, J=6.8 Hz), 1.25-1.30(m, 36H) , 1.44(s, 9H) , 1.49(m, 2H) , 1.59-1.72 (m, 3H) , 1.84(m, 1H) , 2.22(t, 2H, J=7.6 Hz), 3.10(m, 2H) , 3.74(s, 3H) , 4.56-4.63(m, 2H) , 6.01 (d, 1H, J=6.4 Hz) . (1009) ESIMS (m/z): 583.5 ( [M+H] +) .

Reference： [1]Current Patent Assignee: AJINOMOTO COMPANY INC - WO2017/73797, 2017, A1 Location in patent: Paragraph 0169

47
[ 112-85-6 ]
[ 18598-74-8 ]
N-docosanoyl-L-isoleucine methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 18h;Cooling with ice;	To L-isoleucine methyl ester hydrochloride (500 mg, 2.75 mmol) were added N, N-dimethylformamide (28 ml) and behenic acid (1.41 g, 4.13 mmol) at room temperature, and the mixture was cooled in an ice bath. Then, l-ethyl-3- ( 3- dimethylaminopropyl) carbodiimide hydrochloride (792 mg, 4.13 mmol), 1-hydroxybenzotriazole (558 mg, 4.13 mmol), and (1022) triethylamine (1.15 ml, 8.25 mmol) were added, and the mixture was removed from the ice bath and stirred at room temperature for 18 hr. Thereafter, ethyl acetate (70 ml) was added and the mixture was filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give resultant product containing the object product as a main component. (1023) This was dissolved in dichloromethane (70 ml), washed three times with saturated aqueous sodium hydrogen carbonate solution (20 ml), and once with water (30 ml) and 15% brine (30 ml), and the organic layer was concentrated under reduced pressure. Of the residue (886 mg) , 200 mg was taken and purified by PTLC (hexane/ethyl acetate) to give N-docosanoyl-L-isoleucine methyl ester (112 mg, 0.24 mmol, yield 39%) as a white solid. (1024) 1H-NMR (400 MHz, CDC13)5: 0.86-0.94(m, 9H) , 1.11-1.33 (n 37H) , 1.43(m, 1H), 1.63 (m, 2H) , 1.87 (m, 1H) , 2.21(t, 2H, J=7.6 Hz), 3.73(s, 3H) , 4.62(dd, 1H, J=4.8 Hz, 8.8 Hz), 5.91(d, 1H, J=8.4 Hz) . (1025) ESIMS(m/z): 468.4 ( [M+H] +) , 935.9 ( [2 M+H] +) .

Reference： [1]Patent: WO2017/73797,2017,A1 .Location in patent: Paragraph 0171

48
[ 112-85-6 ]
[ 6306-52-1 ]
N-docosanoyl-L-valine methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 18h;Cooling with ice;	To L-valine methyl ester hydrochloride (500 mg, 2.98 mmol) were added N, N-dimethylformamide (29.8 ml) and behenic acid (1.52 g, 4.47 mmol) at room temperature, and the mixture was cooled in an ice bath. Then, l-ethyl-3- (3- dimethylaminopropyl) carbodiimide hydrochloride (857 mg, 4.47 mmol), 1-hydroxybenzotriazole (604 mg, 4.47 mmol), and (1030) triethylamine (1.25 ml, 8.94 mmol) were added, and the mixture was removed from the ice bath and stirred at room temperature for 18 hr. Thereafter, ethyl acetate (70 ml) was added and the mixture was filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) . The obtained solid was slurry washed with diethyl ether (30 ml) to give N- docosanoyl-L-valine methyl ester (331 mg, 0.73 mmol, yield 25%) as a white solid. (1031) 1H-NMR (400 MHz, CDC13)5: 0.86-0.95(m, 9H) , 1.25-1.33 (m, 36H) , 1.64(m, 2H) , 2.15(dsep, 1H, J=4.8 Hz, 6.8 Hz), 2.23(t, 2H, J=7.6 Hz), 3.74(s, 3H) , 4.59(dd, 1H, J=4.8 Hz, 8.8 Hz), 5.88(d, 1H, J=8.4 Hz) . (1032) ESIMS(m/z): 454.4 ( [M+H] +) , 907.8 ( [2 M+H] +) .

Reference： [1]Patent: WO2017/73797,2017,A1 .Location in patent: Paragraph 0172

49
[ 112-85-6 ]
[ 100422-07-9 ]
[ 70253-78-0 ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium hydroxide; In dichloromethane; at 20℃; for 72h;	The behenic acid (102.2mg, 0.30mmol) and potassium hydroxide (16.8mg, 0.30mmol) mixed, Was added trifluoromethanesulfonic acid trifluoroethyl phenyl trivalent salt (196.3mg, 0.45mmol) in dichloromethane (3mL), the reaction was stirred at room temperature for 72h, Reaction finished, Extraction was carried out with dichloromethane (3 x 3 mL). Dichloromethane solution under reduced pressure by rotary evaporation, The residue was purified by column chromatography (eluent petroleum ether) Collect product segments, Concentrated pumping pump to obtain trifluoroethyl dodecanoate (78% yield).

Reference： [1]Patent: CN106349071,2017,A .Location in patent: Paragraph 0031; 0032

50
[ 123-78-4 ]
[ 112-85-6 ]
[ 27888-44-4 ]

Yield	Reaction Conditions	Operation in experiment
68%	With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 20℃;	The sphingosine (0.1 mmol) was dissolved in 8ml of dry tetrahydrofuran, was added dicyclohexyl carbodiimide (0.11mmol), 1- hydroxybenzotriazole (0.11 mmol), behenic acid (0.11 mmol ), overnight at room temperature, a white solid 42mg, yield: 68%.

Reference： [1]Patent: CN106631871,2017,A .Location in patent: Paragraph 0034-0036; 0039

51
[ 112-85-6 ]
[ 86516-36-1 ]
C₃₈H₆₃N₃O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In water; acetonitrile at 37℃; for 2.5h;

Reference： [1]Jiang, Ruiqi; Jiao, Yu; Zhang, Pei; Liu, Yong; Wang, Xu; Huang, Yin; Zhang, Zunjian; Xu, Fengguo [Analytical Chemistry, 2017, vol. 89, # 22, p. 12223 - 12230]

52
[ 112-85-6 ]
[ 1622988-44-6 ]
(E)-4-(3,5-bis((triisopropylsilyl)oxy)styryl)phenyl docosanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide; at 20℃; for 6h;Inert atmosphere;	Compound 3 (3.00 g, 5.55 mmol) and docosanoic acid also named behenic acid (2.27 g, 6.67 mmol) were partially dissolved in dry DCM (180 mL) and the required amount of dry DMF (55 mL) was added to solubilize the acide entirely. Afterwards, DCC (1.70 g, 8.33 mmol) and DMAP (339 mg, 2.78 mmol) were added and the reaction was stirred at room temperature under argon until the conversion was completed according to TLC. After 6h, the reaction was stored into the fridge (4 C) to allow the formation of DCU precipitate, which was then filtered on frit. DCM (65 mL) was added to the filtrate and it was washed with water (2*150 mL) and brine (150 mL). The organic layer was dried over MgSO4 and evaporated to gain 8.00 g of crude product. Purification was performed by chromatography on silica gel (pentane/EtOAc 99:1) to yield 4a (6.63 g, 76%) as a white solid. Rf (pentane/EtOAc 99:1) 0.4; 1H NMR (500 MHz, CDCl3): deltaH 7.50 (d, J = 8.5 Hz, 2H, H2' and H6'), 7.07 (d, J = 8.5 Hz, 2H, H3' and H5'), 6.99 (d, J = 16.0 Hz, 1 H, H8), 6.92 (d, J = 16.0 Hz, 1 H, H7), 6.65 (d, J = 2.0 Hz, 2H, H2 and H6), 6.36 (t, J = 2.5 Hz, 1 H, H4), 2.56 (t, J = 7.5Hz, 2H, CH2-C=O), 1.76 (quint, J = 7.5 Hz, 2H, CH2-CH2-C=O), 1.43-1.22 (m, 42H, CH2-CH2 and CH-Si), 1.11 (d, J = 7.5 Hz, 36H, CH3-CH), 0.89 (t, J = 7.1 Hz; 3H, CH3-CH2). 13C NMR (126 MHz, CDCl3) deltaC 172.4, 157.2, 157.2, 150.2, 138.9, 135.1, 129.1, 127.7, 127.5 (2C), 121.9 (2C), 111.5(2C), 111.4, 34.6, 32.1, 29.9(8C), 29.8, 29.8, 29.8, 29.7, 29.6, 29.5, 29.4, 29.2, 25.1, 22.8, 18.1 (6C), 14.3, 12.8(12C).

Reference： [1]Bioscience Reports,2018,vol. 38
[2]Patent: EP3482758,2019,A1 .Location in patent: Paragraph 0123

53
[ 112-85-6 ]
(2S)-2-amino-N,N-diheptyl-5-[(N-nitrocarbamimidoyl)amino]pentanamide hydrochloride [ No CAS ]
N-[(1S)-1-(diheptylcarbamoyl)-4-[(N-nitrocarbamimidoyl)amino]butyl]docosanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%		To a dichloromethane solution (10 mL) of behenic acid (241 mg, 0.74 mmol) were added under ice-cooling a catalytic amount of DMF and oxalyl dichloride (108 mg, 0.85 mmol) and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated and the obtained residue was dissolved in THF (2 mL). This was added to a THF solution (10 mL) of (2S)-2-amino-N,N-diheptyl-5-[(N-nitrocarbamimidoyl)amino]pentanamide hydrochloride (350 mg, 0.78 mmol) obtained in step 2 and triethylamine (285 mg, 2.82 mmol) and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated and the obtained residue was purified by silica gel chromatography (dichloromethane/methanol=50/1) to give the title compound (400 mg, yield 77%). 1H-NMR (400 MHz, CDCl3) delta8.74-8.66 (m, 1H), 7.86-7.70 (m, 2H), 6.78 (d, J=8.0 Hz, 1H), 4.88-4.83 (m, 1H), 3.66-3.47 (m, 2H), 3.25-2.99 (m, 1H), 3.25 (t, J=7.6 Hz, 2H), 1.72-1.47 (m, 10H), 1.28-1.17 (m, 52H), 0.95-0.87 (m, 9H).

Reference： [1]Patent: US2018/311342,2018,A1 .Location in patent: Paragraph 1497-1500

54
[ 112-85-6 ]
(2S)-2-amino-N-dodecyl-5-[(N-nitrocarbamimidoyl)amino]pentanamide hydrochloride [ No CAS ]
N-[(1S)-1-(dodecylcarbamoyl)-4-[(N-nitrocarbamimidoyl)amino]butyl]docosanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%		To a dichloromethane solution (20 mL) of behenic acid (1.0 g, 2.94 mmol) were added DMF (0.3 mL) and oxalyl dichloride (0.30 mL, 3.53 mmol) and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated and the obtained residue was dissolved in THF (5 mL). This was added to a THE solution (20 mL) of 15 (2S)-2-amino-N-dodecyl-5-[(N-nitrocarbamimidoyl)amino]pentanamide hydrochloride (1.37 g, 3.23 mmol) obtained in Synthetic Example 1 and 8 triethylamine (1.19 g, 11.76 mmol) and the mixture was stirred at room temperature overnight. 37 Water was added to the reaction mixture, the mixture was stirred at room temperature for 10 min and the obtained solid was washed with water and dried to give the 38 title compound (2.0 g, yield 96%). (1380) 1H-NMR (400 MHz, CDCl3) delta8.88-8.76 (m, 1H), 7.53-7.41 (m, 2H), 6.92-6.81 (m, 2H), 4.80-4.70 (m, 1H), 3.68-3.55 (m, 1H), 3.29-3.12 (m, 3H), 2.24 (t, J=7.6 Hz, 2H), 1.77-1.49 (m, 8H), 1.37-1.19 (m, 54H), 0.88 (t, J=6.8 Hz, 6H)

Reference： [1]Patent: US2018/311342,2018,A1 .Location in patent: Paragraph 1377-1380

55
[ 112-85-6 ]
(2R)-2-amino-3-[[(2R)-2-amino-3-(dodecylamino)-3-oxo-propyl]disulfanyl]-N-dodecyl-propanamide dihydrobromide [ No CAS ]
N-[(1R)-1-[[[(2R)-2-(docosanoylamino)-3-(dodecylamino)-3-oxo-propyl]disulfanyl]methyl]-2-(dodecylamino)-2-oxo-ethyl]docosanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%		Step 3 Synthesis of N-[(1R)-1-[[[(2R)-2-(docosanoylamino)-3-(dodecylamino)-3-oxo-propyl]disulfanyl]methyl]-2-(dodecylamino)-2-oxo-ethyl]docosanamide To a dichloromethane solution (4 mL) of behenic acid (238 mg, 0.7 mmol) were added a catalytic amount of DMF and oxalyl dichloride (196 mg, 1.54 mmol), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated and the obtained residue was dissolved in THF (4 mL). This was added to a THF solution (4 mL) of (2R)-2-amino-3-[[(2R)-2-amino-3-(dodecylamino)-3-oxo-propyl]disulfanyl]-N-dodecyl-propanamide dihydrobromide (200 mg, 0.35 mmol) obtained in step 2, and the mixture was adjust same to pH10-11 by adding 5M aqueous sodium hydroxide solution and stirred at room temperature overnight. To the reaction mixture was added 1N hydrochloric acid to adjust same to pH6-7, and the precipitate was collected by filtration to give the title compound (140 mg, yield 33%). 1H-NMR (400 MHz, THF-d8) delta8.55 (t, J=5.2 Hz, 2H), 8.07 (d, J=9.6 Hz, 2H), 5.65-5.59 (m, 2H), 3.62-3.43 (m, 4H), 3.28-3.12 (m, 3H), 2.61 (t, J=6.4 Hz, 3H), 2.07-1.83 (m, 118H), 1.23 (t, J=6.8 Hz, 12H).

Reference： [1]Patent: US2018/311342,2018,A1 .Location in patent: Paragraph 1614-1616

56
[ 112-85-6 ]
(2S)-2-amino-4-methyl-N-undecyl-pentanamide [ No CAS ]
N-[(1S)-3-methyl-1-(undecylcarbamoyl)butyl]docosanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%		To a DMF solution (10 mL) of behenic acid (998 mg, 2.9 mmol), HOBt (594 mg, 4.4 mmol) and EDCI (840 mg, 4.4 mmol) was added triethylamine (889 mg, 8.8 mmol) and the mixture was stirred at room temperature for 15 min. To the reaction mixture was added (2S)-2-amino-4-methyl-N-undecyl-pentanamide (1.0 g, 3.5 mmol) obtained in step 2 and the mixture was stirred under a nitrogen atmosphere at room temperature overnight. The reaction mixture was poured into water under ice-cooling, and the obtained crude crystals were collected by filtration, washed with water and was purified by silica gel chromatography (dichloromethane/methanol=50/1-20/1) to give the title compound (580 mg, yield 32%). 1H-NMR (400 MHz, CDCl3) delta6.16-6.13 (m, 1H), 5.91-5.89 (d, J=8.8 Hz, 1H), 4.43-4.37 (m, 1H), 3.24-3.18 (m, 2H), 2.19-2.16 (m, 2H), 1.62-1.59 (m, 4H), 1.53-1.46 (m, 3H), 1.25 (m, 52H), 0.94-0.86 (m, 12H).

Reference： [1]Patent: US2018/311342,2018,A1 .Location in patent: Paragraph 1392-1394

57
[ 112-85-6 ]
3-amino-N-dodecyl-2,2-dimethyl-propanamide hydrochloride [ No CAS ]
N-[3-(dodecylamino)-2,2-dimethyl-3-oxo-propyl]docosanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%		Step 3 Synthesis of N-[3-(dodecylamino)-2,2-dimethyl-3-oxo-propyl]docosanamide To a dichloromethane solution (10 mL) of behenic acid (1.0 g, 2.96 mmol) were added DMF (0.2 mL) and oxalyl dichloride (470 mg, 3.7 mmol) and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated and the obtained residue was dissolved in THF (10 mL). This was added to a THF solution (20 mL) of 3-amino-N-dodecyl-2,2-dimethyl-propanamide hydrochloride (1.05 g, 3.7 mmol) obtained in step 2 and triethylamine (1.5 g, 14.8 mmol) and the mixture was stirred at room temperature overnight. The precipitated solid was collected by filtration, methanol (50 mL) was added and the mixture was stirred at 70 C. for 30 min. The mixture was cooled to room temperature and the solid was collected by filtration to give the title compound (946 mg, yield 43%). 1H-NMR (400 MHz, CDCl3) delta6.37 (brs, 1H), 5.86 (brs, 1H), 3.56-3.42 (m, 2H), 3.24-3.19 (m, 2H), 3.18-3.14 (m, 2H), 1.62-1.61 (m, 2H), 1.50-1.49 (m, 2H), 1.25 (m, 54H), 1.18 (s, 6H), 0.88 (t, J=6.8 Hz, 6H).

Reference： [1]Patent: US2018/311342,2018,A1 .Location in patent: Paragraph 1443-1444

58
[ 59578-12-0 ]
[ 112-85-6 ]
2,2',3,3',4,4'-hexa-O-trimethylsilyl-6,6'-di-O-docosanoyl-α,α'-D-trehalose [ No CAS ]
2,2',3,3',4,4'-hexa-O-trimethylsilyl-6-docosanoyl-6'-hydroxy-α,α'-D-trehalose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%; 45%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In toluene; at 70℃; for 168h;	2,2?,3,3?,4,4?-Hexa-O-trimethylsilyl-alpha,alpha?-D-trehalose (0.1 mmol, 1 equiv.) and behenic acid (0.18 mmol, 1.8 equiv.) in dry toluene (5 mL),EDCI (0.20 mmol, 2 equiv.) and DMAP (0.44 mmol, 4.4equiv.) were added and the reaction was stirred at 70 C for seven days. The resulting precipitate was removed by filtration and the precipitate washed thoroughly with EtOAc (2 ×50 mL), the combined organic layers were washed with water(50 mL) and brine (40 mL), dried (MgSO4), filtered and concentratedin vacuo. The products were purified by silica gelflash chromatography (eluting in Hex: EtOAc 20:1) to give2,2?,3,3?,4,4?-hexa-O-trimethylsilyl-6-docosanoyl-6?-hydroxy-alpha,alpha?-D-trehalose (45% yield) and 2,2?,3,3?,4,4?-hexa-O-trimethylsilyl-6,6?-di-O-docosanoyl-alpha,alpha?-D-trehalose(40% yield). Spectral data matched that previously reported[6].

Reference： [1]Glycoconjugate Journal,2019,vol. 36,p. 69 - 78

59
[ 112-85-6 ]
2',3'-di-O-benzyl-L-glycerol-(1'→1)-2,3-di-O-benzyl-β-D-arabinofuran-osyl-(1→2)-3-O-benzyl-5-p-methoxybenzyl-α-D-arabinofuranoside [ No CAS ]
2',3'-di-O-benzyl-L-glycerol-(1'→1)-2,3-di-O-benzyl-5-O-behenate-β-D-arabinofuranosyl-(1→2)-3-O-benzyl-5-p-methoxy-benzyl-α-D-arabinofuranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0℃; for 48h;Inert atmosphere;	EDCI (13.6 mg, 0.070 mmol) in dry CH2Cl2 (1 mL) was addeddropwise to a stirred solution of alpha-D-arabinofuranoside (13) (13.2 mg,0.0142 mmol), DMAP (8.6 mg, 0.070 mmol) and behenic acid (7.1 mg,0.020 mmol) in dry CH2Cl2 (1 mL) at 0 C under nitrogen, and stirredfor 48 h. The precipitate was washed with CH2Cl2 (10 mL). The solventwas evaporated and the residue was purified by chromatographyeluting with hexane/ethyl acetate (5:1) to give compound (19) as acolourless thick oil (15 mg, 85%) [Found (M+NH4)+: 1266.7800;C78H108O13N, requires: 1266.7815], [alpha] D22 -2.2 (c 0.92, CHCl3); deltaH(400 MHz, CDCl3): 7.30 - 7.17 (25H, m), 7.15 (2H, d, J 8.6 Hz), 6.77(2H, d, J 8.6 Hz), 5.00 (1H, br.d, J 4.1 Hz), 4.95 (1H, br.s), 4.61 (1H, d,J 12.1 Hz), 4.60 (2H, br.s), 4.58 (1H, d, J 12.1 Hz), 4.51 (1H, d, J11.6 Hz), 4.46 - 4.41 (3H, m), 4.37 (3H, br.d, J 11.7 Hz), 4.36 (1H, d, J11.7 Hz), 4.25 (1H, br.d, J 1.9 Hz), 4.17 - 4.10 (2H, m), 4.07 - 3.98(3H, m), 3.95 (1H, br.q, J 6.6 Hz), 3.89 (1H, br.dd, J 2.4, 6.0 Hz), 3.80(1H, dd, J 5.1, 10.4 Hz), 3.74 - 3.68 (4H, incl. s at 3.72 for OCH3), 3.57- 3.50 (3H, incl. br. dd, J 5.0, 8.5 Hz at 3.53), 3.49 - 3.42 (2H, incl. br.dd J 4.2, 11.1 Hz at 3.47), 2.13 (2H, dt, J 3.6, 7.7 Hz), 1.53 - 1.02 (38H,m), 0.81 (3H, t, J 6.7 Hz); deltaC (101 MHz, CDCl3): 173.4, 159.2, 138.7,138.3, 138.0, 137.8, 137.5, 130.2, 129.4, 128.5, 128.4, 128.3, 128.2,128.0, 127.9, 127.8, 127.7, 127.65, 127.6, 127.55, 127.5, 127.4, 113.7,106.0, 100.5, 85.9, 84.4, 83.8, 82.6, 81.5, 78.9, 77.0, 73.4, 72.9, 72.5,72.4, 72.3, 72.2, 70.3, 69.6, 67.2, 66.0, 55.2, 34.0, 31.9, 29.8, 29.7,29.65, 29.6, 29.5, 29.4, 29.3, 29.1, 24.8, 22.7, 14.1; numax: 3062, 3031,2924, 2859, 1741, 1612, 1513, 1454, 1248, 1110,738, 699 cm-1.

Reference： [1]Chemistry and Physics of Lipids,2019,vol. 221,p. 207 - 218

60
[ 112-85-6 ]
[ 480-39-7 ]
5-hydroxy-4-oxo-2-phenylchroman-7-yl docosanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%		General procedure: A solution of fatty acid (1 eq) in dichloromethane (DCM) at 0 C was added of N,N'-dicyclohexylcarbodiimide (DCC) (1.2 eq) and a catalytic amount of 4-dimethylaminopyridine (DMAP); the obtained mixture was vigorously stirred for 30 min. Then, a solution of pinocembrin in DCM was dripped slowly and the reaction was stirred for 24 h. The reaction progress was monitored by TLC. The mixture was filtered on Celite with DCM; the filtrate was then washed with a cold solution of NaHCO 3 to remove any trace of free acid. The obtained organic layer was then washed with brine and evaporated under reduced pressure to furnish the desired product.

Reference： [1]Natural Product Research,2018,p. 1 - 7

61
[ 112-85-6 ]
(2R,3R,11bR)-dihydrotetrabenazine [ No CAS ]
(2R,3R,11bR)-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1a]isoquinolin-2-ylbehenate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%		ehenicacid (240.1 mg, 0.71 mmol) and 4-dimethylaminopyridine (DMAP) (22.9 mg, 0.19 mmol) were dissolved in the mixture of anhydrous CH2CI2 (4 mL) and THF (2ml_) and 1-Ethyl-3-(3-dimethyaminopropy)carbodiimide (EDC) (166.4 uL, 0.94 mmol) was added to the previous solution under an inert environment. The mixture was stirred at room temperature for 5-10 min. The (2R,3R,11bR)-3-isobutyl-9,10-dimethoxy- 1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-ol (150 mg, 0.47 mmol) dissolved in anhydrous CH2CI2 (2 mL) was subsequently added to the previous mixture under an inert environment. The reaction mixture was stirred at room temperature overnight and then concentrated. The purification of resulted compound was via flash column chromatography (Rf= 0.15 at EA/Hex = 1/5) and gave 116 mg of compound 1-2 in 39% yield. NMR (400 MHz, CDCb): 0.84-0.90 (m, 9H), 0.98-1.04 (m, 1 H), 1.23-1.41 (m, 36H), 1.44-1.49 (dd, 1H), 1.60-1.66 (m, 4H), 1.93-2.08 (m, 2H), 2.30-2.34 (m, 2H), 2.44-2.63 (m, 3H), 2.95-3.16 (m, 2H), 3.19 (d, 1H), 3.82 (s, 6H), 4.61-4.66 (m, 1H), 6.55 (s, 1H), 6.60 (s, 1H). ESI-MS [M+H] calcd: 642.5; Found [M+H]: 642.5

Reference： [1]Patent: WO2019/94491,2019,A1 .Location in patent: Paragraph 0070; 0071

62
[ 626-89-1 ]
[ 112-85-6 ]
4-methylpentyl behenate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 25℃; Inert atmosphere;

Reference： [1]Dekić, Biljana R.; Ristić, Milenko N.; Mladenović, Marko Z.; Dekić, Vidoslav S.; Ristić, Novica R.; Ranđelović, Vladimir; Radulović, Niko S. [Chemistry and biodiversity, 2019, vol. 16, # 7]

63
[ 112-85-6 ]
2',3'-di-O-benzyl-L-glycerol-(1'→1)-2,3-di-O-benzyl-5-O-methanesulfonyl-α-D-arabinofuranosyl-(1→3)-[2,3-di-O-benzyl-5-O-methanesulfonyl-α-D-arabinofuranosyl-(1→5)]-2-O-benzyl-α-D-arabinofuranoside [ No CAS ]
2',3'-di-O-benzyl-L-glycerol-(1'→1)-2,3-di-O-benzyl-5-O-behenate-α-D-arabinofuranosyl-(1→3)-[2,3-di-O-benzyl-5-O-behenate-α-Darabinofuranosyl-(1→5)]-2-O-benzyl-α-D-arabinofuranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With cesium bicarbonate; In tetrahydrofuran; N,N-dimethyl-formamide; at 70℃; for 72h;Inert atmosphere;	(a) CsHCO3 (0.076 g, 0.39 mmol) was added to a stirred solution of dimesylate (10) (0.05 g, 0.03mmol) and behenic acid (0.03 g, 0.09 mmol) in dry DMF:THF (1:5, 1 mL) at rt under nitrogen. Themixture was stirred at 70 C for 3 days, then diluted with EtOAc (25 mL) and water (5 mL). Theaqueous layer was re-extracted with EtOAc (2 × 10 mL). The combined organic layers were washedwith water (5 mL) and brine (5 mL), dried and evaporated under reduced pressure to give a thick oil;column chromatography eluting with petrol/EtOAc (3:1) gave 2',3'-di-O-benzyl-L-glycerol-(1'?1)-2,3-di-O-benzyl-5-O-behenate-alpha-D-arabinofuranosyl-(1?3)-[2,3-di-O-benzyl-5-O-behenate-alpha-Darabinofuranosyl-(1?5)]-2-O-benzyl-alpha-D-arabinofuranoside (11, R = Bn) as a colourless thick oil (55mg, 80%) [MALDI: Found (M + Na)+: 1786.1; C111H158NaO17 requires: 1786.1], [alpha] 22D +36 (c 1.0, CHCl3)which showed deltaH (400 MHz, CDCl3): 7.31-7.11 (35H, m), 5.09 (1H, br. s), 5.06 (1H, br. s), 4.97 (1H, br.s), 4.59 (2H, br. s), 4.51-4.35 (10H, m), 4.33 (1H, d, J 11.8 Hz), 4.26 (1H, d, J 11.8 Hz), 4.20 (1H, br. dd,J 3.3, 7.3 Hz), 4.12 (6H, br. m), 4.04 (1H, br. dd, J 2.8, 6.9 Hz), 4.00 (1H, br. d, J 2.5 Hz), 3.95-3.89 (2H,m), 3.84 (1H, dd, J 4.3, 11.8 Hz), 3.81-3.76 (2H, incl. br. dd, J 4.1, 8.5 Hz at 3.78), 3.75 (1H, br. d, J 3.4Hz), 3.74-3.68 (1H, p, J 5.0 Hz), 3.66 (1H, br. dd, J 2.1, 11.7 Hz), 3.58-3.49 (3H, incl. br. q, J 4.6 Hz at3.53), 2.17 (4H, t, J 7.6 Hz), 1.56-1.00 (76H, m), 0.81 (6H, t, J 6.8 Hz); deltaC (101 MHz, CDCl3): 173.6, 173.5,138.6, 138.3, 137.7, 137.6, 137.5, 137.4, 137.3, 128.5, 128.4, 128.35, 128.3, 128.0, 127.95, 127.9, 127.85,127.8, 127.75, 127.7, 127.65, 127.6, 127.5, 106.5, 106.2, 105.5, 88.3, 88.2, 88.1, 83.4, 83.3, 80.8, 80.3, 79.2,78.9, 76.9, 73.4, 72.3, 72.2, 72.1, 72.0, 71.9, 71.7, 70.3, 67.1, 65.6, 63.3, 63.2, 34.1, 34.0, 31.9, 29.7, 29.6, 29.5,29.4, 29.35, 29.3, 29.2, 24.8, 22.7, 14.1; numax: 3064, 3031, 2923, 2853, 1740, 1718, 1455, 1066, 698 cm-1.

Reference： [1]Molecules,2019,vol. 24

64
[ 112-85-6 ]
[ 56-81-5 ]
[ 18641-57-1 ]

Yield	Reaction Conditions	Operation in experiment
	at 250℃; for 15h; Inert atmosphere;	4 [Synthesis Example 4] Glyceryl Tribehenate Under a nitrogen atmosphere, 340 g of behenic acid and 31.5 g of glycerol were reacted by heating at 250° C. for 15 hours while the water that was produced was removed, thus obtaining a monoester of Synthesis Example 4. The amount of monoester having a total of 40 to 48 carbon atoms within the obtained monoester was 0.0% by mass.

Reference： [1]Current Patent Assignee: STATE UNIVERSITY SYSTEM OF FLORIDA - US2019/307672, 2019, A1 Location in patent: Paragraph 0092

65
[ 112-92-5 ]
[ 112-85-6 ]
[ 24271-12-3 ]

Yield	Reaction Conditions	Operation in experiment
97%	With triphenylphosphine-sulfur trioxide adduct In neat (no solvent) at 110℃; for 2h; Green chemistry;	Esterification General procedure: In order to perform the esterification reaction, into a single-necked reaction flask, at equivalent quantities stearic acid (0.50 g, 1.76 mmol) and myristyl alcohol (0.48 g, 1.77 mmol) were added. After addition of the catalyst (5 mg), the mixture was heated with stirring in an oil bath at 110 C (bath temperature) for 2 h. Finally the reaction mixture was cooled and the obtained solid was crystallized from methanol/acetone/tetrahydrofuran to afford pure crystalline product.
92.8%	at 250℃; for 15h; Inert atmosphere;	2 [Synthesis Example 2] Stearyl Behenate Under a nitrogen atmosphere, 340 g of behenic acid and 270 g of stearyl alcohol were reacted by heating at 250° C. for 15 hours while the water that was produced was removed, thus obtaining a monoester of Synthesis Example 2. The amount of monoester having a total of 40 to 48 carbon atoms within the obtained monoester was 92.8% by mass.

Reference： [1]Yıldırım, Ayhan; Kıraylar, Kaan [Phosphorus, Sulfur and Silicon and the Related Elements, 2020, vol. 196, # 4, p. 407 - 413]
[2]Current Patent Assignee: STATE UNIVERSITY SYSTEM OF FLORIDA - US2019/307672, 2019, A1 Location in patent: Paragraph 0090

66
[ 112-85-6 ]
[ 99755-59-6 ]
rotigotine behenate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69.0%		34.1 g (0.1 mol) of behenic acid was dissolved in 300 ml of dichloromethane (DCM) under nitrogen at room temperature, and 12.7 g (0.1 mol) of oxalyl chloride was added dropwise to the mixed solution; the resulting solution after completion of the reaction was referred to as Solution I. 31.5 g (0.1 mol) of rotigotine was dissolved in a mixed solution containing 15.2 g (0.15 mol) of triethylamine and 300 ml of dichloromethane (DCM), which was referred to as Solution II. Solution I was added dropwise to Solution II to provide a reaction solution, upon completion of the reaction, the reaction solution was washed with an equal volume of water, and the solvent of the organic phase was evaporated under reduced pressure. The residue was purified by column chromatography, with a 1:3 (v/v) ethyl acetate-petroleum ether system as the eluent, to give a white solid (44.2 g) in a yield of 69.0%, melting point 48-52 C. are the 1H NMR and the 13C NMR spectra of the titled compound, respectively, and is the IR spectrum of the titled compound. 1H NMR (CDCl3, 400 MHz) deltaH: 7.12 (m, 2H, H-7 & H-14), 6.98 (d, J=7.40 Hz, 1H, H-6), 6.92 (q, J=3.44, 5.04 Hz, 1H, H-15), 6.82 (d, J=7.28 Hz, 2H, H-8 & H-13), ?3.01 (m 4H, H-1 & H-4), 2.81 (m, 4H, H-19 & H-20), 2.54 (m, 5H, H-2, H-16 & H-22), 2.08 (m, 1H, H-3), 1.76 (m, 2H, H-23), 1.58 (m, 1H, H-3), 1.39 (m, 2H, H-41), 1.26 (m, 36H, H-17, H-24?H-40), 0.88 (m, 6H, H-18 & H-42); 13C NMR (CDCl3, 100 MHz) deltaC: 172.0 (C-21), 148.9 (C-5), 143.1 (C-12), 138.8 (C-9), 128.7 (C-10), 127.1 (C-15), 126.5 (C-7), 126.2 (C-13), 124.5 (C-14), 123.1 (C-8), 119.0 (C-6), 56.4 (C-2), 52.6 (2C, C-19 & C-16), 34.2 (C-22), 32.1 (C-40), 31.9 (C-20), 30.1 (C-1), 29.2-29.7 (C-24?C-39), 25.3 (C-3), 25.1 (C-23), 24.1 (C-4), 22.7 (C-41), 22.3 (C-17), 14.1 (C-42), 11.9 (C-18).

Reference： [1]Patent: US2019/330177,2019,A1 .Location in patent: Paragraph 0038-0041

67
[ 7483-59-2 ]
[ 112-85-6 ]
1-(4-(2,3-dihydroxypropyl)-1-piperazinyl)-docosanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68.6%		To a 1 L 4-neck flask equipped with a stirrer and condenser6.8 g (0.02 mol) of behenic acid,32.6 g (0.27 mol) of thionyl chloride, thenAfter heating under reflux in a nitrogen stream for 16 hours, excess thionyl chloride was removed by distillation.Subsequently, into the obtained reaction product,9.7 g (0.06 mol) of 3- (1-piperazinyl) -1,2-propanediol, 50.1 g of isopropanol,And 2.3 g (0.02 mol) of sodium carbonate,At 110 C in a nitrogen stream,Aged for 72 hours. afterwards,The reaction solution was concentrated with an evaporator,Perform chloroform extraction,Concentrate to dryness,White solid1- [4- (2,3-dihydroxypropyl) -1-piperazinyl] -docosanone7.7 g (68.6% yield) were obtained.

Reference： [1]Patent: JP2019/189567,2019,A .Location in patent: Paragraph 0097-0101

68
[ 687-64-9 ]
[ 112-85-6 ]
C₅₁H₁₀₀N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 60℃; for 16h;	To a stirred solution of 01-35-2 (5 g, 0.0312 mol) in DMF (100 mL) at RT was added slowly DIPEA (32 mL, 0.1872 mol), linear fatty acid 01-35-1 (31.8 g, 0.0936 mol), and HATU (41.5 g, 0.1092 mol). The resulting mixture was stirred at 60 C. After 16 h, the reaction mixture was quenched with ice water, the solids isolated by filtration, and then the solids dried under vacuum. Purification of the solids by trituration with THF yielded 01-35-3 as an off-white solid (7 g, 28%).

Reference： [1]Patent: WO2019/232255,2019,A1 .Location in patent: Paragraph 0578

69
[ 112-85-6 ]
[ 23277-43-2 ]
3-(cyclobutylmethyl)-4a,7-dihydroxy-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl docosanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%		EDCI (0.56 g, 2.9 mmol) was added to behenic acid (1.0 g, 2.9 mmol) in THF (50 mL) at 0 C. with stirring. The reaction mixture was stirred for 30 min and Nalbuphine hydrochloride (1.16 g, 2.9 mmol), trimethylamine (0.29 g, 2.9 mmol) and 4-dimethylaminopyidine (0.12 g, 1.0 mmol) were added at 0 C. The stirring was continued for 1 h at 0 C. and at room temperature overnight. The reaction mixture was filtered, filtrate was evaporated, and the residue was purified by column chromatography (silicagel, EtOAc/Heptanes, 1:2). The white solid was formed after evaporation of selected fractions, yield 1.45 g (73%), purity 97% by HPLC. The structure was confirmed by NMR 1H. Synthesis and properties of NB-39 was also described in U.S. Pat. No. 5,750,534.

Reference： [1]Patent: US2020/55864,2020,A1 .Location in patent: Paragraph 0086

70
[ 112-85-6 ]
[ 126550-86-5 ]
1-O-(α-Gal-4-β-Gal-4-β-Glc)ceramide d18:1/C22:0 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sphingolipid ceramide N-deacylase; In aq. acetate buffer; at 37℃; for 1.5h;pH 5.5;Enzymatic reaction;	General procedure: Individual Gb3 molecules were synthesized by the reverse reaction of SCDase with purified lyso-Gb3 or its analogs and purchased fatty acids. The preparations LG3, LG3(-2), and LG3(+18) described in Fig. 3 were used as purified lyso-Gb3, lyso-Gb3(-2), and lyso-Gb3(+18), respectively. For example, when a Gb3 isoform Gb3(d18:1)(C18:0) was synthesized, LG3 and stearic acid was used. Approximately 0.5 mug of LG3 was mixed with 25mug of stearic acid dissolved in CHCl3/MeOH (2:1 (v/v)) and dried. Lipids were suspended in 40 mul of enzyme mixture (5 mug/ml of SCDase in 25 mM sodium acetate buffer (pH 5.5) containing 0.5% Triton X-100, 5 mM CaCl2, and 5% DMSO) and incubated at 37 C for 1.5 h. The reaction was stopped by the addition of 0.8 ml of CHCl3/MeOH (2:1 (v/v)), and aqueous lipids were separated by the addition of 0.2 ml of 1.5% FA in H2O and centrifugation at 6500xg for 5 min. After removal of the upper layer, the product was recovered in the lower layer and designated as LG3/C18:0. In a manner similar to Gb3 isoforms, when Gb3 analogs Gb3(-2) and Gb3(+18) containing stearic acid were synthesized, LG3(-2) and LG3(+18) were used, respectively. All synthesized Gb3 standards were adjusted to concentrations at 3,000 peak area when determined by UPLC-MS/MS. In the direct assay, Gb3(d18:2)(C17:0) was used as an internal standard, which was synthesized enzymatically from LG3(-2) and heptadecanoic acid by the same method as described above.

Reference： [1]Journal of Biological Chemistry,2020,vol. 295,p. 5577 - 5587

71
[ 112-85-6 ]
C₃₆H₆₉NO₁₈ [ No CAS ]
C₅₈H₁₁₁NO₁₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sphingolipid ceramide N-deacylase; In aq. acetate buffer; at 37℃; for 1.5h;pH 5.5;Enzymatic reaction;	General procedure: Individual Gb3 molecules were synthesized by the reverse reaction of SCDase with purified lyso-Gb3 or its analogs and purchased fatty acids. The preparations LG3, LG3(-2), and LG3(+18) described in Fig. 3 were used as purified lyso-Gb3, lyso-Gb3(-2), and lyso-Gb3(+18), respectively. For example, when a Gb3 isoform Gb3(d18:1)(C18:0) was synthesized, LG3 and stearic acid was used. Approximately 0.5 mug of LG3 was mixed with 25mug of stearic acid dissolved in CHCl3/MeOH (2:1 (v/v)) and dried. Lipids were suspended in 40 mul of enzyme mixture (5 mug/ml of SCDase in 25 mM sodium acetate buffer (pH 5.5) containing 0.5% Triton X-100, 5 mM CaCl2, and 5% DMSO) and incubated at 37 C for 1.5 h. The reaction was stopped by the addition of 0.8 ml of CHCl3/MeOH (2:1 (v/v)), and aqueous lipids were separated by the addition of 0.2 ml of 1.5% FA in H2O and centrifugation at 6500xg for 5 min. After removal of the upper layer, the product was recovered in the lower layer and designated as LG3/C18:0. In a manner similar to Gb3 isoforms, when Gb3 analogs Gb3(-2) and Gb3(+18) containing stearic acid were synthesized, LG3(-2) and LG3(+18) were used, respectively. All synthesized Gb3 standards were adjusted to concentrations at 3,000 peak area when determined by UPLC-MS/MS. In the direct assay, Gb3(d18:2)(C17:0) was used as an internal standard, which was synthesized enzymatically from LG3(-2) and heptadecanoic acid by the same method as described above.

Reference： [1]Journal of Biological Chemistry,2020,vol. 295,p. 5577 - 5587

72
[ 112-85-6 ]
[ 29836-26-8 ]
octyl 6-O-behenoyl-β-D-glucoside [ No CAS ]

Reference： [1]Chemical Communications,2020,vol. 56,p. 4292 - 4295

73
[ 849585-22-4 ]
[ 112-85-6 ]
behenyl lactylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With Na2CO3 supported on 4A zeolite solid phase composite catalyst; In water; at 30 - 200℃; under 7.50075 - 75.0075 Torr; for 7h;	Put 307kg of 88% lactic acid into the reactor, stir at 30 C, evacuate to a pressure of 1kPa, hold for 1h, put in 300kg of behenic acid, stir for 1h, and put in 10kg of Na2CO3 supported on 4A zeolite, The temperature is raised to 200 C, the reaction is carried out at a pressure of 10kPa for 6h, the catalyst is filtered and recovered, the temperature is lowered, and the material is discharged.Get behenyl lactic acid product.The content of behenic acid in the product was determined, and the conversion rate was calculated to be 85.9%.

Reference： [1]Patent: CN111072471,2020,A .Location in patent: Paragraph 0028

74
[ 49715-04-0 ]
[ 112-85-6 ]
docosanoic acid chloromethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%		To a solution of behinic acid (2.93 mmol, 1.00 g) in DCM :H20 (18:12 mL) at room temperature was added NaHCOs ( 0.99 g, 11.8 mmol), followed by tetrabutylammonium hydrogen sulfate (0.293 mmol, 0.098 g). The mixture was cooled to 0C and allowed to stir for 15 minutes, followed by the addition of chloromethyl chlorosulfate (3.82 mmol, 0.386 mL). Slow gas evolution was observed. After 18 hours, the reaction mixture was diluted with H2O and CH2CI2. The organic and aqueous layers were separated, and the aqueous layer was washed with CH2CI2 (2 x 20 mL). The combined organic layers were washed with brine, dried over Na2SC>4, filtered, and concentrated in vacuo. The residue was purified on a 40 g silicel column eluting with 0-25% EtOAc in hexanes. The fractions containing the desired product were concentrated in vacuo to yield docosanoic acid chloromethyl ester 1.054 g (92 %). XH NM R (CHLOROFORM-d) d: 5.72 (br d, J=10.4 Hz, 2H), 2.37 (br t, J=7.7 Hz, 2H), 1.53-1.81 (m, 2H), 1.25 (s, 36H), 0.87 (br t, J=6.3 Hz, 3H).

Reference： [1]Patent: WO2020/77038,2020,A1 .Location in patent: Page/Page column 60

75
[ 112-53-8 ]
[ 112-85-6 ]
[ 42233-07-8 ]

Yield	Reaction Conditions	Operation in experiment
89%	With triphenylphosphine-sulfur trioxide adduct In neat (no solvent) at 110℃; for 2h; Green chemistry;	Esterification General procedure: In order to perform the esterification reaction, into a single-necked reaction flask, at equivalent quantities stearic acid (0.50 g, 1.76 mmol) and myristyl alcohol (0.48 g, 1.77 mmol) were added. After addition of the catalyst (5 mg), the mixture was heated with stirring in an oil bath at 110 C (bath temperature) for 2 h. Finally the reaction mixture was cooled and the obtained solid was crystallized from methanol/acetone/tetrahydrofuran to afford pure crystalline product.

Reference： [1]Yıldırım, Ayhan; Kıraylar, Kaan [Phosphorus, Sulfur and Silicon and the Related Elements, 2020, vol. 196, # 4, p. 407 - 413]

76
[ 112-72-1 ]
[ 112-85-6 ]
[ 42233-09-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	With triphenylphosphine-sulfur trioxide adduct In neat (no solvent) at 110℃; for 2h; Green chemistry;	Esterification General procedure: In order to perform the esterification reaction, into a single-necked reaction flask, at equivalent quantities stearic acid (0.50 g, 1.76 mmol) and myristyl alcohol (0.48 g, 1.77 mmol) were added. After addition of the catalyst (5 mg), the mixture was heated with stirring in an oil bath at 110 C (bath temperature) for 2 h. Finally the reaction mixture was cooled and the obtained solid was crystallized from methanol/acetone/tetrahydrofuran to afford pure crystalline product.

Reference： [1]Yıldırım, Ayhan; Kıraylar, Kaan [Phosphorus, Sulfur and Silicon and the Related Elements, 2020, vol. 196, # 4, p. 407 - 413]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	112-85-6	MDL No. :	MFCD00002807
Formula :	C₂₂H₄₄O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UKMSUNONTOPOIO-UHFFFAOYSA-N
M.W :	340.58	Pubchem ID :	8215
Synonyms :	Behenic acid;C22:0 Fatty acid	Chemical Name :	Docosanoic acid (Chunks or pellets or flakes)

Num. heavy atoms :	24
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.95
Num. rotatable bonds :	20
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	109.64
TPSA :	37.3 Å²

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-1.01 cm/s

Log Po/w (iLOGP) :	5.26
Log Po/w (XLOGP3) :	10.37
Log Po/w (WLOGP) :	7.89
Log Po/w (MLOGP) :	5.58
Log Po/w (SILICOS-IT) :	7.89
Consensus Log Po/w :	7.4

[ CAS No. 112-85-6 ] {[proInfo.proName]}

Quality Control of [ 112-85-6 ]

Related Doc. of [ 112-85-6 ]

Product Details of [ 112-85-6 ]

Calculated chemistry of [ 112-85-6 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 112-85-6 ]

Application In Synthesis of [ 112-85-6 ]

[ 112-85-6 ] Synthesis Path-Upstream 1~1

[ 112-85-6 ] Synthesis Path-Downstream 1~76

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	1.0
Ghose :	None
Veber :	1.0
Egan :	1.0
Muegge :	2.0
Bioavailability Score :	0.56

Log S (ESOL) :	-7.16
Solubility :	0.0000233 mg/ml ; 0.0000000684 mol/l
Class :	Poorly soluble
Log S (Ali) :	-11.1
Solubility :	0.0000000027 mg/ml ; 0.0 mol/l
Class :	Insoluble
Log S (SILICOS-IT) :	-7.7
Solubility :	0.00000675 mg/ml ; 0.0000000198 mol/l
Class :	Poorly soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	3.0

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling