[ CAS No. 19420-57-6 ] {[proInfo.proName]}

Name: 19420-57-6|(R)-2-Hydroxy-3-(stearoyloxy)propyl (2-(trimethylammonio)ethyl) phosphate|98%
Brand: Ambeed
SKU: A685884
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Quality Control of [ 19420-57-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 19420-57-6 ]

Product Details of [ 19420-57-6 ]

CAS No. :	19420-57-6	MDL No. :	MFCD00050427
Formula :	C₂₆H₅₄NO₇P	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IHNKQIMGVNPMTC-RUZDIDTESA-N
M.W :	523.68	Pubchem ID :	497299
Synonyms :		Chemical Name :	(R)-2-Hydroxy-3-(stearoyloxy)propyl (2-(trimethylammonio)ethyl) phosphate

Safety of [ 19420-57-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 19420-57-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 19420-57-6 ]

[ 19420-57-6 ] Synthesis Path-Downstream 1~65

1
[ 132194-61-7 ]
[ 19420-57-6 ]
[ 132194-62-8 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1990,p. 1281 - 1282
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1992,vol. 31,p. 824 - 827
[3]Angewandte Chemie,1992,vol. 104,p. 1386 - 1387

2
[ 171597-35-6 ]
[ 19420-57-6 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1990,p. 1281 - 1282
[2]Angewandte Chemie,1992,vol. 104,p. 1386 - 1387
[3]Tetrahedron Asymmetry,1997,vol. 8,p. 451 - 458

3
[ 19420-57-6 ]
[ 154436-47-2 ]
[ 160593-72-6 ]

Reference： [1]Bioscience, Biotechnology and Biochemistry,1994,vol. 58,p. 1927 - 1928

4
[ 19420-57-6 ]
[ 55726-27-7 ]
[ 35418-57-6 ]

Reference： [1]Tetrahedron Asymmetry,1997,vol. 8,p. 451 - 458

5
[ 302-79-4 ]
[ 19420-57-6 ]
1-stearoyl-2-all-trans-retinoyl-glycero-3-phosphorylcholine [ No CAS ]

Reference： [1]Synthetic Communications,1998,vol. 28,p. 2945 - 2958

6
[ 816-94-4 ]
[ 19420-57-6 ]

Yield	Reaction Conditions	Operation in experiment
99%	With tris hydrochloride; sodium docusate; calcium chloride; In 2,2,4-trimethylpentane; at 40℃; for 0.5h;pH 8.5;Enzymatic reaction;	General procedure: Hydrolysis of 1,2-diacyl-sn-glycero-3-phosphocholines 2a-e was carried out according to the method described by Morgado et al.[30] Two solutions, A: 0.635 mmol of 2a-e in 13.2 mL isooctane, and B: 174 mg (0.393 mmol) of sodium docusate (AOT) in 13.2mL isooctane, were pre-incubated for 0.5 h at 40 C on a magnetic stirrer. Then, 262 mL of PLA2 (10000 U mL-1; 1 U is equivalent to the amount of enzyme producing 1 mmole of free fatty acid per minute at pH 8 and 40 C) and the same volume of Tris-HCl buffer (0.1 M, pH 8.5) with 0.75M of CaCl2 were then added to solution B and the reaction was started by adding solution A. The progress of the enzymatic reactions was monitored by TLC (65 : 25 : 4 CHCl3/CH3OH/H2O v/v/v). The reaction was carried out for 30 min. The enzyme was separated from the reaction mixture using diatomaceous earth (Celite 545) and the solvent was evaporated to dryness at 40 Cunder vacuum. 1-Acyl LPCs 3a-e were purified on a silica gelcolumn (65 : 25 : 4 CHCl3/CH3OH/H2O v/v/v). Product containing fractions of Rf 0.3 were collected and solvent evaporated under vacuum (45 C).

Reference： [1]Australian Journal of Chemistry,2015,vol. 68,p. 1065 - 1075
[2]Journal of Materials Chemistry,2000,vol. 10,p. 1047 - 1059
[3]Chemistry and Physics of Lipids,1998,vol. 95,p. 1 - 9

7
[ 19420-57-6 ]
8-methylstearoyl anhydride [ No CAS ]
1-stearoyl-2-(8-methylstearoyl)-sn-glycero-3-phosphatidylcholine [ No CAS ]

Reference： [1]Chemistry and Physics of Lipids,1998,vol. 95,p. 1 - 9

8
[ 19420-57-6 ]
15-oxoeicosatetraenoic acid [ No CAS ]
C₄₆H₈₂NO₉P [ No CAS ]
C₄₆H₈₂NO₉P [ No CAS ]

Reference： [1]Journal of Chemical Research - Part S,1999,p. 500 - 501

9
[ 19420-57-6 ]
[ 264874-85-3 ]
[ 264874-86-4 ]

Reference： [1]Journal of Mass Spectrometry,2000,vol. 35,p. 224 - 236

10
[ 19420-57-6 ]
[ 264874-80-8 ]
[ 264874-81-9 ]

Reference： [1]Journal of Mass Spectrometry,2000,vol. 35,p. 224 - 236

11
[ 19420-57-6 ]
[ 125943-49-9 ]
[ 110511-57-4 ]

Reference： [1]Journal of Materials Chemistry,2000,vol. 10,p. 1047 - 1059

12
[ 19420-57-6 ]
(4Z,7Z,10Z,13Z,15E,19Z)-17-(1-Methoxy-1-methyl-ethylperoxy)-docosa-4,7,10,13,15,19-hexaenoic acid [ No CAS ]
[ 351525-54-7 ]

Reference： [1]Angewandte Chemie - International Edition,2001,vol. 40,p. 1755 - 1757

13
[ 19420-57-6 ]
[ 31385-36-1 ]
[ 477202-46-3 ]
C₃₉H₇₂NO₉P [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2002,p. 1941 - 1943

14
[ 108-30-5 ]
[ 19420-57-6 ]
1-stearoyl-2-succinyl-glycerophosphocholine [ No CAS ]

Reference： [1]Chemistry and Physics of Lipids,2003,vol. 126,p. 29 - 38

15
[ 19420-57-6 ]
[ 33812-63-4 ]
[ 477202-46-3 ]

Reference： [1]Chemistry and Physics of Lipids,2004,vol. 131,p. 81 - 92

16
[ 910545-48-1 ]
[ 19420-57-6 ]
C₅₆H₈₆N₁₁O₁₅P [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2006,vol. 54,p. 832 - 835

17
[ 28319-77-9 ]
[ 112-76-5 ]
[ 19420-57-6 ]

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 2974 - 2978
[2]Langmuir,2018,vol. 34,p. 13368 - 13374

18
[ 85647-89-8 ]
[ 19420-57-6 ]

Reference： [1]Tetrahedron Asymmetry,1997,vol. 8,p. 451 - 458
[2]Journal of the Chemical Society. Chemical communications,1990,p. 1281 - 1282

19
[ 57-11-4 ]
[ 19420-57-6 ]

Reference： [1]Tetrahedron Asymmetry,1997,vol. 8,p. 451 - 458

20
[ 171505-41-2 ]
[ 19420-57-6 ]

Reference： [1]Tetrahedron Asymmetry,1997,vol. 8,p. 451 - 458

21
[ 171505-42-3 ]
[ 19420-57-6 ]

Reference： [1]Tetrahedron Asymmetry,1997,vol. 8,p. 451 - 458

22
1-stearoyl-2,5,6-tribenzyl-3,4-isopropylidene-D-mannitol [ No CAS ]
[ 19420-57-6 ]

Reference： [1]Tetrahedron Asymmetry,1997,vol. 8,p. 451 - 458

23
1-stearoyl-2,5,6-tribenzyl-D-mannitol [ No CAS ]
[ 19420-57-6 ]

Reference： [1]Tetrahedron Asymmetry,1997,vol. 8,p. 451 - 458

24
[ 19420-57-6 ]
[ 154436-51-8 ]

Reference： [1]Bioscience, Biotechnology and Biochemistry,1994,vol. 58,p. 1927 - 1928

25
[ 19420-57-6 ]
[ 154436-48-3 ]

Reference： [1]Bioscience, Biotechnology and Biochemistry,1994,vol. 58,p. 1927 - 1928

26
[ 19420-57-6 ]
1-stearoyl-2-<(5'Z,8'Z,11'Z,13'E,S)-hydroxy-5',8',11',13'-icosatetraenoyl>-sn-glycero-3-phosphoserine [ No CAS ]

Reference： [1]Bioscience, Biotechnology and Biochemistry,1994,vol. 58,p. 1927 - 1928

27
[ 19420-57-6 ]
1-stearoyl-2-<(5'Z,8'Z,11'Z,13'E,S)-hydroperoxy-5',8',11',13'-icosatetraenoyl>-sn-glycero-3-phosphoserine [ No CAS ]

Reference： [1]Bioscience, Biotechnology and Biochemistry,1994,vol. 58,p. 1927 - 1928

28
[ 111-63-7 ]
[ 19420-57-6 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1992,vol. 31,p. 824 - 827
[2]Journal of the Chemical Society. Chemical communications,1990,p. 1281 - 1282

29
[ 19420-57-6 ]
[ 132194-63-9 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1992,vol. 31,p. 824 - 827
[2]Journal of the Chemical Society. Chemical communications,1990,p. 1281 - 1282

30
2,2,2-trifluoroethyl octadecanoate [ No CAS ]
[ 19420-57-6 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1992,vol. 31,p. 824 - 827

31
[ 55357-38-5 ]
[ 19420-57-6 ]

Reference： [1]Angewandte Chemie,1992,vol. 104,p. 1386 - 1387

32
[ 19420-57-6 ]
[ 143447-34-1 ]

Reference： [1]Angewandte Chemie,1992,vol. 104,p. 1386 - 1387

33
[ 19420-57-6 ]
[ 143447-35-2 ]

Reference： [1]Angewandte Chemie,1992,vol. 104,p. 1386 - 1387

34
[ 19420-57-6 ]
[ 143447-37-4 ]

Reference： [1]Angewandte Chemie,1992,vol. 104,p. 1386 - 1387

35
[ 19420-57-6 ]
[ 143447-36-3 ]

Reference： [1]Angewandte Chemie,1992,vol. 104,p. 1386 - 1387

36
[ 28319-77-9 ]
[ 818-08-6 ]
[ 112-67-4 ]
[ 19420-57-6 ]
C₂₆H₅₄NO₇P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 2: Stearoyl-lyso-PC A suspension of 0.5 g of GPC, 0.5 g of DBTO (1 eq), and 10 ml of methanol was stirred at reflux until a clear solution was obtained (1 hr); the solvent was evaporated from the solution to give a residual volume of 1 ml. 5 ml of IPA was added, the mixture was concentrated again at ordinary pressure to give a residual volume of 1 ml, and 5 ml of IPA was added. 0.324 ml of TEA (1.2 eq) and 0.62 g of palmitoyl chloride (1.2 eq) were dropped in at 25C. At the end of the dropping, the conversion (31P-NMR) was 92%, and the ratio between the two forms of lyso-PC was 1:9 in favour of the compound acylated at position sn-1.

Reference： [1]Patent: EP1650215,2006,A1 .Location in patent: Page/Page column 7

37
cis-9,trans-11-octadecadienoic acid [ No CAS ]
[ 19420-57-6 ]
1-octadecanoyl-2-(9Z,11E)-octadecadienoyl-sn-glycero-3-phosphocholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 48h;Inert atmosphere; Darkness;	General procedure: Compounds 4c-e were prepared from 1-stearoyl-2-hydroxysn-glycero-3-phosphocholine (3a) (100 mg, 0.191 mmol) by adding 106 mg (0.381 mmol) of a mixture of CLA isomers (1c), cis-9,trans-11 (1d) or trans-10,cis-12 CLA (1e) dissolved in 5.7mL of anhydrous CH2Cl2, DMAP (53.8 mg, 0.191 mmol), and finally a solution of DCC (119 mg, 0.419 mmol) in 1.9 mL of CH2Cl2. The reaction was carried out for 48 h under a nitrogen atmosphere in the dark and at ambient temperature. The precipitate that was formed in the reaction mixture was removed using a Shott funnel. Ion-exchange resin (Dowex 50W X8, Hform) was added to the filtrate and the mixture was stirred for 30 min to dislodge DMAP. The Dowex resin was filtered off and the solvent was evaporated under vacuum. The crude PC was purified on a silica gel column (65 : 25 : 4 CHCl3/CH3OH/H2O v/v/v). Product-containing fractions of Rf 0.4 were collected and solvent evaporated under vacuum (45 C).

Reference： [1]Australian Journal of Chemistry,2015,vol. 68,p. 1065 - 1075

38
trans-10,cis-12-octadecadienoic acid [ No CAS ]
[ 19420-57-6 ]
1-octadecanoyl-2-(10E,12Z)-octadecadienoyl-sn-glycero-3-phosphocholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 48h;Inert atmosphere; Darkness;	General procedure: Compounds 4c-e were prepared from 1-stearoyl-2-hydroxysn-glycero-3-phosphocholine (3a) (100 mg, 0.191 mmol) by adding 106 mg (0.381 mmol) of a mixture of CLA isomers (1c), cis-9,trans-11 (1d) or trans-10,cis-12 CLA (1e) dissolved in 5.7mL of anhydrous CH2Cl2, DMAP (53.8 mg, 0.191 mmol), and finally a solution of DCC (119 mg, 0.419 mmol) in 1.9 mL of CH2Cl2. The reaction was carried out for 48 h under a nitrogen atmosphere in the dark and at ambient temperature. The precipitate that was formed in the reaction mixture was removed using a Shott funnel. Ion-exchange resin (Dowex 50W X8, Hform) was added to the filtrate and the mixture was stirred for 30 min to dislodge DMAP. The Dowex resin was filtered off and the solvent was evaporated under vacuum. The crude PC was purified on a silica gel column (65 : 25 : 4 CHCl3/CH3OH/H2O v/v/v). Product-containing fractions of Rf 0.4 were collected and solvent evaporated under vacuum (45 C).

Reference： [1]Australian Journal of Chemistry,2015,vol. 68,p. 1065 - 1075

39
[ 51660-44-7 ]
[ 19420-57-6 ]
C₁₈-DP-VPA [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73.8%		5 ml of reaction flask was added 190 g of C18-<strong>[19420-57-6]lysophosphatidylcholine</strong>, 9.5 g of 4-dimethylaminopyridine (DMAP) and 260 g of valproic acid anhydride to 60 C for 4 h. The solution was clarified and cooled to 20 C The volume of acetone, dropping, cooled to 0 C for 2 h, suction, vacuum drying at 50 C, the resulting crude product in the 5L reaction flask by adding 1.1 times the volume of anhydrous ethanol 20 C stirring dissolved, dropping 12.5 times the volume of acetone , The residue was cooled to 0 C for 2 h, filtered, and vacuum dried at 50 C to obtain 174 g of C18-DP-VPA in a yield of 73.8% and a purity of 99.2%.

Reference： [1]Patent: CN104230981,2016,B .Location in patent: Paragraph 0008; 0020; 0023; 0027-0028

40
[ 28319-77-9 ]
[ 112-76-5 ]
[ 19420-57-6 ]

Yield	Reaction Conditions	Operation in experiment
83.3%		(1) Preparation of choline glycerophosphate dibutyltin oxide complex: 30 g (0.1 lmol) of choline glycerophosphate was dissolved in 500 ml of absolute ethanol, added with 24.9 g (0.1 mol) of dibutyltin oxide, heated to reflux for 0.5 hours, cooled to room temperature, filtered, wash the filter cake with anhydrous isopropanol to the filtrate without choline glycerophosphate, and dry the filter cake under vacuum at 60 C to obtain 50.6 g of white choline glycerophosphate dibutyltin oxide complex. (2) Under stirring, 25.3 g (0.05 mol) of glycerophosphocholine-dibutyltin oxide complex was placed in 3000 ml of tetrahydrofuran, 6 g (0.059 mol) of triethylamine, 16 g (0.053 mol) of stearic acid chloride , Stirred at 50 C for 3 hours, after the reaction was completed, cooled to room temperature, 200 ml of distilled water was added and stirred for 0.5 hours, filtered and the filtrate was concentrated under reduced pressure to give 25 g crude stearyl lysolecithin. [0016] The crude product of 25 g stearyl lysolecithin was recrystallized from a mixture of acetonitrile-ethanol in a volume ratio of 100: 1 to obtain 22.5 g of stearyl lysolecithin product with a yield of 83.3% and a purity of 98.1 %.

Reference： [1]Patent: CN106810574,2017,A .Location in patent: Paragraph 0014-0016

41
camptothecin-20-Osn-glycerol-3-phosphocholine-(3, 3’-dithiodipropionyl) monoester [ No CAS ]
[ 19420-57-6 ]
1-stearoyl-2-(camptothecin-20-O-(3,3'-dithiodipropionyl)monoester) glycerol-3-phosphocholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%		0.540 g (0.001 mol) of camptothecin-20-0-(3, 3’-dithiodipropionyl) monoester was dissolved into 200 ml of dichloromethane, add 0.5 g of 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride, 0.1 g of 4-dimethylaminopyridine, at room temperature, after stirring for 3 hours add 0.523 g (0.001 mol) of 1-stearoyl-Sn-glycerol-3-phosphocholine, at room temperature, after stirring for 72 hours, the reaction solution was poured into 500 ml of ice water, filtered, at 50 C, vacuum drying the filter cake, the filter cake was subjected to silica gel column chromatography (methanol: chloroform: water = 25:65:2), obtained yellow 1-stearoyl-2-(camptothecin-20-0-(3, 3dithiodipropionyl) monoester) glycerol-3-phosphocholine 0.21 g (i.e. phospholipids analogue), yield 20%.
20%		0.540 g (0.001 mol) of camptothecin-20-O-(3,3'-dithiodipropionyl)monoester was dissolved in 50 ml of dimethyl sulfoxide, and 0.5 g of 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride, 0.1 g of 4-dimethylaminopyridine, stirred at room temperature for 3 hours, then added 0.523 g (0.001 mol) of 1-stearoyl-sn-glycerol-3-phosphocholine, room temperature after stirring for 72 hours, the reaction liquid was poured into 500 ml of ice water, filtered, and the filter cake was dried under vacuum at 50 C, and the filter cake was subjected to silica gel column chromatography (methanol: chloroform: water = 25:65:2). yellow 1-stearoyl-2-(camptothecin-20-O-(3,3'-dithiodipropionyl) monoester)glycerol-3-phosphocholine 0.21 g (ie lecithin analog) in 20% yield.

Reference： [1]Patent: CN108586535,2018,A .Location in patent: Paragraph 0024-0025
[2]Patent: CN108774264,2018,A .Location in patent: Paragraph 0061

42
FAAzo-4 [ No CAS ]
[ 19420-57-6 ]
C₄₂H₆₈N₃O₈P [ No CAS ]
C₄₂H₆₈N₃O₈P [ No CAS ]

Reference： [1]Langmuir,2018,vol. 34,p. 13368 - 13374

43
C₂₄H₁₅F₃N₄O₄ [ No CAS ]
[ 19420-57-6 ]
C₅₀H₆₇F₃N₅O₁₀P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In chloroform; at 20℃; for 72h;	(4) 500 mg (1.04 mM) of the compound 3 prepared in the step (3) was dissolved in 20 ml of alcohol-free chloroform, and then 400 mg (2.08 mM) of EDC.HCL was added, respectively. 254mg (2.08mM) DMAP, 281 mg (2.08 mM) of HOBT and 545 mg (1.04 mM) of lyso-PC, After reacting at room temperature for 72 h, After the reaction, the product is separated and purified by thin layer chromatography. Use a thick preparation plate (20*20cm, coating thickness 0.4-0.5mm), The developing agent is a mixed solution of dichloromethane and methanol, The ratio of dichloromethane to methanol was 10:1, and an off-white solid was obtained. That is, the compound 4 is fluorinated fluorescent phospholipid, and the yield is about 32%.

Reference： [1]Patent: CN108690079,2018,A .Location in patent: Paragraph 0051; 0065-0068
[2]Chemical Communications,2020,vol. 56,p. 14427 - 14430

44
[ 60-33-3 ]
[ 19420-57-6 ]
[ 27098-24-4 ]

Yield	Reaction Conditions	Operation in experiment
77%	With dmap; dicyclohexyl-carbodiimide; In chloroform; at 20℃; for 120h;	Intermediate 2 (300 mg, 0.57 mmol) was dissolved in CHCh (10 mL), then fatty acid (1.15 mmol), 4-DMAP (140 mg, 1.15 mmol) and DCC (236 mg, 1.15 mmol) were added. The reaction mixture was stirred at 20 C for 5 days, the solids were filtered and washed with CHCh. The solvent was evaporated and the residue was chromatographed on silica in CHCh, CHCh- MeOH (2: 1, 1 : 1, 1 :2) and MeOH. The pure fractions were evaporated to give product as a colorless waxy substance. Rf 0.40 (CHCh, MeOH, cone. M 13 :5: 1). (0237) [0160] l-Acyl-2-linoleyl-sn-glycero-3-phosphatidylcholine (3a). Yield 344 mg (77%). NMR (CDCh) d 5.36 (m, 4H), 4.41 (m, 1H), 4.30 (m, 2H), 4.11 (dd, J= 12.1, 7.4 Hz, (0238) 1H), 4.00-3.85 (m, 2H), 3,76 (m, 2H), 3.33 (m, 9H), 2.80 (m, 2H), 2.28 (m, 4H), 2.10 (m, 4H), 1.58 (m, 4H), 1.24 (m, 40H), 0.97 (m, 6H).

Reference： [1]FEBS Journal,2019,vol. 286,p. 2099 - 2117
[2]Patent: WO2020/102596,2020,A1 .Location in patent: Paragraph 0158; 0159-0160

45
[ 19420-57-6 ]
11,11-dideutero-cis,cis-octadeca-9,12-dienoic acid [ No CAS ]
1-stearoyl-2-(11,11-d2-linoleyl)-sn-glycero-3-phosphatidylcholine [ No CAS ]

Reference： [1]FEBS Journal,2019,vol. 286,p. 2099 - 2117

46
[ 506-32-1 ]
[ 19420-57-6 ]
[ 35418-59-8 ]

Reference： [1]FEBS Journal,2019,vol. 286,p. 2099 - 2117

47
[7,7,10,10,13,13-D₆]arachidonic acid [ No CAS ]
[ 19420-57-6 ]
1-stearoyl-2-(7,7,10,10,13,13-d6-arachidonoyl)-sn-glycero-3-phosphatidylcholine [ No CAS ]

Reference： [1]FEBS Journal,2019,vol. 286,p. 2099 - 2117

48
[ 463-40-1 ]
[ 19420-57-6 ]
[ 35418-57-6 ]

Yield	Reaction Conditions	Operation in experiment
77%	With 1-methyl-1H-imidazole; 2-methyl-6-nitrobenzoic anhydride; In dichloromethane; at 20℃; for 16h;	To a solution of alpha-linolenic acid (1h) (55 mg, 0.198 mmol) in CH2Cl2 (2 mL) were added NMI (0.036 mL, 0.456 mmol) and MNBA (158 mg, 0.459 mmol). After 20 min of stirring at rt, lyso-PC 2a (53 mg, 0.101 mmol) was added. The mixture was stirred at rt for 16 h and concentrated to give a residue, which was purified by chromatography on silica gel (CHCl3/MeOH/H2O = 65:25:1 to 65:25:3) to afford PC 3h (61 mg, 77%): Rf = 0.08(CHCl3/MeOH/H2O = 65:25:1); 1H NMR (400 MHz, CD3OD) delta 0.90 (t, J = 7.2 Hz, 3 H),0.97 (t, J = 7.2 Hz, 3 H), 1.21-1.43 (m), 1.54-1.68 (m, 4 H), 2.02-2.14 (m, 4 H), 2.31 (t, J =7.6 Hz, 2 H), 2.34 (t, J = 7.6 Hz, 2 H), 2.81 (t, J = 6.0 Hz, 4 H), 3.22 (s, 9 H), 3.61-3.68 (m,2 H), 4.00 (t, J = 6.2 Hz, 2 H), 4.17 (dd, J = 12.1, 6.8 Hz, 1 H), 4.23-4.32 (m, 2 H), 4.44 (dd,J = 12.1, 3.0 Hz, 1 H), 5.20-5.27 (m, 1 H), 5.27-5.44 (m, 6 H); 13C NMR (100 MHz, CD3OD)delta 13.2, 13.4, 20.2, 22.4, 24.7, 25.1, 25.2, 26.9, 28.8, 28.90, 28.94, 29.0, 29.2, 29.35, 29.42,29.5, 31.7, 33.6, 33.7, 53.3 (t, J = 3.4 Hz, 3 C), 59.1 (d, J = 4.6 Hz), 62.2, 63.5 (d, J = 4.6Hz), 66.0 (m), 70.4 (d, J = 8.4 Hz), 126.9, 127.5, 127.8, 127.9, 129.7, 131.4, 173.0, 173.4;HRMS (FAB) calcd for C44H83O8NP [(M+H)+] 784.5856, found 784.5893.

Reference： [1]Synlett,2020,vol. 31,p. 718 - 722
[2]FEBS Journal,2019,vol. 286,p. 2099 - 2117

49
[ 1300023-51-1 ]
[ 19420-57-6 ]
1-stearoyl-2-(11,11,14,14-D4-linolenyl)-sn-glycero-3-phosphatidylcholine [ No CAS ]

Reference： [1]FEBS Journal,2019,vol. 286,p. 2099 - 2117

50
[ 19420-57-6 ]
[ 134863-32-4 ]
1-stearoyl-2-(14,14-D2-linolenyl)-sn-glycero-3-phosphatidylcholine [ No CAS ]

Reference： [1]FEBS Journal,2019,vol. 286,p. 2099 - 2117

51
6,6,9,9,12,12,15,15,18,18-D₁₀-docosahexaenoic acid [ No CAS ]
[ 19420-57-6 ]
1-stearoyl-2-(6,6,9,9,12,12,15,15,18,18-d10-docosahexaenoyl)-sn-glycero-3-phosphatidylcholine [ No CAS ]

Reference： [1]FEBS Journal,2019,vol. 286,p. 2099 - 2117

52
7,7,10,1013,13,16,16-D₈-eicosapentaenoic acid [ No CAS ]
[ 19420-57-6 ]
1-stearoyl-2-(7,7,10,10,13,13,16,16-D8-eicosapentaenoyl)-sn-glycero-3-phosphatidylcholine [ No CAS ]

Reference： [1]FEBS Journal,2019,vol. 286,p. 2099 - 2117

53
4-[3-(4-methoxybenzyl)oxiran-2-yl]butanoic acid [ No CAS ]
[ 19420-57-6 ]
C₄₀H₇₀NO₁₀P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With 1-methyl-1H-imidazole; 2-methyl-6-nitrobenzoic anhydride; In dichloromethane; at 20℃; for 24h;Inert atmosphere;	To a solution of acid 1a (48 mg, 0.192 mmol) in CH2Cl2 (1 mL)were added NMI (0.034 mL, 0.43 mmol) and MNBA (148 mg,0.430 mmol). After 20 min of stirring at rt, lyso-PC 2a (50 mg,0.0955 mmol) was added. The mixture was stirred at rt for 24 hunder nitrogen and concentrated to give a residue, which waspurified by chromatography on silica gel (CHCl3/MeOH/H2O =65:25:1 to 65:25:3) to afford PC 3a (63 mg, 87%): Rf = 0.21(CHCl3/MeOH/H2O = 65:25:3). 1H NMR (400 MHz, CD3OD): =0.89 (t, J = 6.8 Hz, 3 H), 1.27 (br s), 1.53-1.88 (m, 6 H), 2.30 (t, J =7.4 Hz, 2 H), 2.43-2.52 (m, 2 H), 2.72-2.83 (m, 2 H), 3.01 (dt, J =7.2, 4.2 Hz, 1 H), 3.10-3.16 (m, 1 H), 3.21 (s, 9 H), 3.60-3.66 (m,2 H), 3.76 (s, 9 H), 4.02 (t, J = 6.2 Hz, 2 H), 4.18 (dd, J = 12.0, 6.4Hz, 1 H), 4.23-4.31 (m, 2 H), 4.44 (dd, J = 12.0, 2.8 Hz, 1 H),5.22-5.29 (m, 1 H), 6.86 (dd, J = 8.4 Hz, 2 H), 7.19 (d, J = 8.4 Hz, 2H). 13C NMR (100 MHz, CD3OD): = 13.1, 21.70, 21.73, 22.3,24.6, 26.9, 28.8, 29.0, 29.1, 29.2, 29.4, 31.7, 32.9, 33.19, 33.21,33.4, 53.3 (t, J = 3.8 Hz, 3 C), 54.2, 56.81 and 56.84, 57.50 and57.53, 59.1 (d, J = 5.3 Hz), 62.2, 63.5 (d, J = 4.6 Hz), 66.0 (m), 70.6(d, J = 7.6 Hz), 113.6, 129.4, 129.8, 158.5, 172.8, 173.6. HRMS(FAB): m/z calcd for C40H71O10NP [M + H]+ 756.4816; found:756.4826.

Reference： [1]Synlett,2020,vol. 31,p. 718 - 722

54
8-[3-[(R)-2-[(tert-butyldimethylsilyl)oxy]octyl]oxiran-2-yl]octanoic acid [ No CAS ]
[ 19420-57-6 ]
1-stearoyl-2-[8-[3-[(R)-2-((tert-butyldimethylsilyl)oxy)octyl]oxiran-2-yl]octanoyl]-sn-glycero-3-phosphorylcholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With 1-methyl-1H-imidazole; 2-methyl-6-nitrobenzoic anhydride; In dichloromethane; at 20℃; for 18h;	To a solution of acid 1b (62 mg, 0.145 mmol) in CH2Cl2 (1.5 mL) were added NMI (0.026mL, 0.33 mmol) and MNBA (115 mg, 0.334 mmol). After 20 min of stirring at rt, lyso-PC2a (38 mg, 0.073 mmol) was added. The mixture was stirred at rt for 18 h and concentratedto give a residue, which was purified by chromatography on silica gel (CHCl3/MeOH/H2O =65:25:1 to 65:25:3) to afford 3b (50 mg, 74%): Rf = 0.25 (CHCl3/MeOH/H2O = 65:25:3); 1HNMR (400 MHz, CD3OD) δ 0.081, 0.084, 0.088, and 0.092 (4 s, total 6 H), 0.87-0.94 (m, 15H), 1.26-1.78 (m), 2.31 (t, J = 7.4 Hz, 2 H), 2.35 (t, J = 7.4 Hz, 2 H), 2.88-2.98 (m, 1 H),3.02-3.10 (m, 1 H), 3.23 (s, 9 H), 3.61-3.68 (m, 2 H), 3.85-3.94 (m, 1 H), 4.00 (t, J = 6.2Hz, 2 H), 4.17 (dd, J = 12.0, 6.8 Hz, 1 H), 4.23-4.32 (m, 2 H), 4.44 (dd, J = 12.0, 3.2 Hz, 1H), 5.21-5.28 (m, 1 H); 13C NMR (100 MHz, CD3OD) δ -5.6, -5.5, 13.2, 17.6, 22.3, 22.4,24.62, 24.64, 25.06, 25.10, 25.2, 26.3, 27.7, 27.8, 28.7, 28.9, 29.0, 29.13, 29.15, 29.2, 29.3,29.4, 29.5, 31.67, 31.74, 33.5, 33.7, 34.98, 35.04, 37.0, 37.6, 53.3 (t, J = 3.4 Hz, 3 C), 53.8and 54.4, 56.2 and 57.1, 59.1 (d, J = 4.5 Hz), 62.3, 63.5 (d, J = 5.3 Hz), 66.0 (m), 70.3, 70.4(d, J = 9.9 Hz), 173.0, 173.4; HRMS (FAB) calcd for C50H101O10NPSi [(M+H)+] 934.6932,

Reference： [1]Synlett,2020,vol. 31,p. 718 - 722

55
[ 19420-57-6 ]
[ 129049-76-9 ]
C₅₀H₁₀₀NO₉PSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With 1-methyl-1H-imidazole; 2-methyl-6-nitrobenzoic anhydride; In dichloromethane; at 20℃; for 19h;	To a solution of acid 1d (84 mg, 0.204 mmol) in CH2Cl2 (2 mL) were added NMI (0.036 mL,0.452 mmol) and MNBA (159 mg, 0.462 mmol). After 20 min of stirring at rt, lyso-PC 2a (50 mg, 0.0955 mmol) was added. The mixture was stirred at rt for 19 h and concentrated togive a residue, which was purified by chromatography on silica gel (CHCl3/MeOH/H2O =65:25:1 to 65:25:3) to afford 3d (70 mg, 80%): Rf = 0.30 (CHCl3/MeOH/H2O = 65:25:3); 1HNMR (400 MHz, CD3OD) δ 0.06 (s, 3 H), 0.07 (s, 3 H), 0.87-0.94 (m, 15 H), 1.24-1.48 (m),1.54-1.66 (m, 4 H), 1.99-2.10 (m, 2 H), 2.12-2.26 (m, 2 H), 2.31 (t, J = 7.4 Hz, 2 H), 2.34(t, J = 7.2 Hz, 2 H), 3.22 (s, 9 H), 3.61-3.66 (m, 2 H), 3.66-3.74 (m, 1 H), 4.00 (t, J = 6.0Hz, 2 H), 4.17 (dd, J = 12.1, 7.0 Hz, 1 H), 4.23-4.32 (m, 2 H), 4.44 (dd, J = 12.1, 2.8 Hz, 1H), 5.20-5.28 (m, 1 H), 5.35-5.48 (m, 2 H); 13C NMR (100 MHz, CD3OD) δ -5.5, -5.3, 13.2,17.6, 22.37, 22.43, 24.67, 24.69, 25.15, 25.17, 27.2, 28.86, 28.93, 29.0, 29.1, 29.2, 29.3, 29.4,29.48, 29.53, 31.74, 31.77, 33.6, 33.7, 35.0, 36.6, 53.3 (t, J = 3.8 Hz, 3 C), 59.1 (d, J = 5.4Hz), 62.3, 63.5 (d, J = 5.3 Hz), 66.0 (m), 70.4 (d, J = 7.6 Hz), 72.3, 125.7, 131.0, 173.0,173.3; HRMS (FAB) calcd for C50H101O9NPSi [(M+H)+] 918.6983, found 918.6964.

Reference： [1]Synlett,2020,vol. 31,p. 718 - 722

56
(18R,5Z,8Z,11Z,14Z,16E)-18-[(tert-butyldimethylsilyl)oxy]icosa-5,8,11,14,16-pentaenoic acid [ No CAS ]
[ 19420-57-6 ]
1-stearoyl-2-[(18R,5Z,8Z,11Z,14Z,16E)-18-((tert-butyldimethylsilyl)oxy)icosa-5,8,11,14,16-pentaenoyl]-sn-glycero-3-phosphorylcholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With 1-methyl-1H-imidazole; 2-methyl-6-nitrobenzoic anhydride; In dichloromethane; at 20℃; for 30h;	To a solution of acid 1f (29 mg, 0.067 mmol) in CH2Cl2 (1 mL) were added NMI (0.024 mL,0.30 mmol) and MNBA (102 mg, 0.296 mmol). After 20 min of stirring at rt, lyso-PC 2a (17mg, 0.0319 mmol) was added. The mixture was stirred at rt for 30 h and concentrated to afford a residue, which was purified by chromatography on silica gel (CHCl3/MeOH/H2O =65:25:1 to 65:25:3) to afford 3f (28 mg, 90%): Rf = 0.23 (CHCl3/MeOH/H2O = 65:25:3); 1HNMR (400 MHz, CD3OD) δ 0.04 (s, 3 H), 0.07 (s, 3 H), 0.89 (t, J = 7.2 Hz, 3 H), 0.90 (t, J= 7.2 Hz, 3 H), 0.92 (s, 9 H), 1.12 (br s), 1.48-1.74 (m, 6 H), 2.09-2.17 (m, 2 H), 2.31 (t, J= 7.4 Hz, 2 H), 2.38 (t, J = 7.4 Hz, 2 H), 2.83 (t, J = 5.8 Hz, 2 H), 2.86 (t, J = 5.8 Hz, 2 H),2.93-3.00 (m, 2 H), 3.22 (s, 9 H), 3.61-3.68 (m, 2 H), 3.94-4.06 (m, 2 H), 4.13-4.22 (m, 2H), 4.23-4.33 (m, 2 H), 4.44 (dd, J = 12.0, 2.8 Hz, 1 H), 5.21-5.28 (m, 1 H), 5.32-5.43 (m,7 H), 5.64 (dd, J = 15.1, 6.2 Hz, 1 H), 5.99 (t, J = 11.1 Hz, 1 H), 6.53 (dd, J = 15.1, 11.1 Hz,1 H); 13C NMR (100 MHz, CD3OD) δ -5.9, -5.4, 8.7, 13.1, 17.7, 22.4, 24.5, 24.6, 25.1, 25.2,25.6, 26.1, 28.8, 29.09, 29.12, 29.3, 29.4, 30.8, 31.7, 33.1, 33.5, 53.3 (t, J = 3.5 Hz, 3 C),59.1 (d, J = 3.8 Hz), 62.2, 63.5 (d, J = 3.0 Hz), 66.0 (m), 70.4 (d, J = 6.8 Hz), 74.2, 124.3,127.5, 127.7, 127.9, 128.0, 128.57, 128.59, 128.7, 136.7, 172.9, 173.4; HRMS (FAB) calcdfor C52H96O9NPSiNa [(M+Na)+] 960.6490, found 960.6475.

Reference： [1]Synlett,2020,vol. 31,p. 718 - 722

57
8-phenylocta-5,7-diynoic acid [ No CAS ]
[ 19420-57-6 ]
C₄₀H₆₄NO₈P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With 1-methyl-1H-imidazole; 2-methyl-6-nitrobenzoic anhydride; In dichloromethane; at 20℃; for 20h;	To a solution of acid 1j (24 mg, 0.113 mmol) in CH2Cl2 (1 mL) were added NMI (0.020 mL,0.25 mmol) and MNBA (88 mg, 0.256 mmol). After 20 min of stirring at rt, lyso-PC 2a (30mg, 0.057 mmol) was added. The mixture was stirred at rt for 20 h and concentrated to give a residue, which was purified by chromatography on silica gel (CHCl3/MeOH/H2O = 65:25:1to 65:25:3) to afford 3j (33 mg, 77%): Rf = 0.13 (CHCl3/MeOH/H2O = 65:25:3); 1H NMR (400 MHz, CD3OD) δ 0.90 (t, J = 6.8 Hz, 3 H), 1.27 (br s), 1.53-1.67 (m, 2 H), 1.88 (quint.,J = 7.2 Hz, 2 H), 2.34 (t, J = 7.2 Hz, 2 H), 2.47 (t, J = 7.0 Hz, 2 H), 2.51 (t, J = 7.2 Hz, 2 H),3.22 (s, 9 H), 3.61-3.67 (m, 2 H), 3.97-4.07 (m, 2 H), 4.20 (dd, J = 12.0, 6.8 Hz, 1 H), 4.23-4.32 (m, 2 H), 4.45 (dd, J = 12.0, 3.4 Hz, 1 H), 5.22-5.30 (m, 1 H), 7.30-7.40 (m, 3 H), 7.43-7.49 (m, 2 H); 13C NMR (100 MHz, CD3OD) δ 14.5, 19.5, 23.8, 24.7, 26.0, 30.2, 3047, 30.50,30.7, 30.8, 33.1, 33.8, 34.9, 54.7 (t, J = 3.4 Hz, 3 C), 60.5 (d, J = 4.6 Hz), 63.5, 64.9 (d, J =5.4 Hz), 66.6, 67.5 (m), 72.1 (d, J = 7.6 Hz), 75.0, 75.8, 84.2, 123.2, 129.6, 130.2, 133.5,173.8, 175.0; HRMS (FAB) calcd for C40H65O8NP [(M+H)+] 718.4448, found 718.4443.

Reference： [1]Synlett,2020,vol. 31,p. 718 - 722

58
[ 10417-94-4 ]
[ 19420-57-6 ]
C₄₆H₈₂NO₈P [ No CAS ]