Name: 13423-48-8|Heptyltriphenylphosphonium bromide|97%
Brand: Ambeed
SKU: A537207
Price: 17.0 USD
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1
[ 694-54-2 ]
[ 13423-48-8 ]
[ 40642-38-4 ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: triphenylheptylphosphonium bromide With potassium hexamethylsilazane In tetrahydrofuran; toluene at 0℃; for 1.08333h; Inert atmosphere; Stage #2: tetrahydro-2H-2-pyranol In tetrahydrofuran; toluene at -78 - 20℃; Inert atmosphere; stereoselective reaction;
	With sodium hydride; dimethyl sulfoxide

Reference： [1]Location in patent: experimental part Ragoussis, Valentine; Perdikaris, Stamatis; Karamolegkos, Antonis; Magkiosi, Konstantina [Journal of Agricultural and Food Chemistry, 2008, vol. 56, # 24, p. 11929 - 11932]
[2]Ohloff,G. et al. [Helvetica Chimica Acta, 1977, vol. 60, p. 1161 - 1174]

2
[ 1931-63-1 ]
[ 13423-48-8 ]
[ 1120-25-8 ]

Yield	Reaction Conditions	Operation in experiment
91.52%	Stage #1: triphenylheptylphosphonium bromide With sodium amide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 1.5h; Stage #2: methyl ester of azelaic acid aldehyde In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -73 - 20℃;
	(i) K, HMPT, (ii) /BRN= 1766823/; Multistep reaction;
	With sodium amide 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT; Yield given. Multistep reaction;

1.7 g

With potassium carbonate In toluene for 4h; Reflux;

Reference： [1]Sarkar; Prasad; Nandy, Sonia [Journal of the Indian Chemical Society, 2005, vol. 82, # 5, p. 475 - 476]
[2]Bestmann; Stransky; Vostrowsky; Range [Chemische Berichte, 1975, vol. 108, # 11, p. 3582 - 3595]
[3]Narasimhan, S.; Mohan, H. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1995, vol. 34, # 11, p. 950 - 953]
[4]Majee [Journal of the Indian Chemical Society, 2012, vol. 89, # 10, p. 1435 - 1438]

3
[ 3433-16-7 ]
[ 13423-48-8 ]
[ 56219-10-4 ]

Yield	Reaction Conditions	Operation in experiment
	(i) K, HMPT, (ii) /BRN= 1769505/; Multistep reaction;
	With sodium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; for 2h; stereoselective reaction;

Reference： [1]Bestmann; Stransky; Vostrowsky; Range [Chemische Berichte, 1975, vol. 108, # 11, p. 3582 - 3595]
[2]Mostyn, Shannon N.; Carland, Jane E.; Shimmon, Susan; Ryan, Renae M.; Rawling, Tristan; Vandenberg, Robert J. [ACS Chemical Neuroscience, 2017, vol. 8, # 9, p. 1949 - 1959]

4
[ 629-04-9 ]
[ 603-35-0 ]
[ 13423-48-8 ]

Yield	Reaction Conditions	Operation in experiment
99%	In acetonitrile for 24h; Heating;
96%	In toluene for 48h; Reflux;
96%	In toluene for 48h; Reflux;

95%	In toluene for 48h; Reflux;
91%	In various solvent(s) Heating;
90%	In toluene at 115℃; Inert atmosphere;
89%	In benzonitrile at 140℃;
89.3%	In o-xylene Heating;
75%	In toluene
75%	In toluene Reflux;
	In xylene
	In toluene for 24h; Heating;
	In N,N-dimethyl-formamide at 105 - 110℃; for 26 - 30h;	1 Preparation of (E3,Z5)-3,5-dodecadienyl methoxymethyl etherTriphenylphosphine (105.02 g, 0.40 mol), n-heptyl bromide (76.93 g, 0.43 mol) and N,N-dimethylformamide (82.0 g) were placed in a reactor and stirred at 105 to 110° C. for 26 to 30 hours. After stirring, the reaction mixture was cooled to 20° C. and tetrahydrofuran (370.0 g) and potassium t-butoxide (42.10 g, 0.375 mol) were added thereto successively at 10 to 15° C. The resulting mixture was stirred at 20° C. for one hour. After stirring, the reaction mixture was cooled to -20° C. and 4-formyl-(E3)-3-butenyl methoxymethyl ether (52.47 g, 0.364 mol) was added dropwise thereto at -15 to -5° C.After dropwise addition was over, the temperature of the mixture was raised to the range of 20 to 25° C. over one hour and then the mixture was stirred as it was for one hour. Then water (200 g) was added thereto to terminate the reaction. The reaction mixture was extracted with toluene (200 g). The organic phase was washed with water and then concentrated under reduced pressure by removing toluene.After concentration, n-hexane (250 g) was added and triphenylphosphine oxide thus precipitated was separated by filtration. The filtrate was concentrated under reduced pressure again and the concentrate was distilled under reduced pressure to yield intended (E3,Z5)-3,5-dodecadienyl methoxymethyl ether (bp: from 82 to 86° C. [1 mmHg], 52.98 g, 0.23 mol) in a yield of 65.2%.Gas chromatography (DB-5: 30 m×0.25 mm, temperature elevation from 150° C. to 280° C. at a rate of 10° C./min) revealed that as a result of the Wittig reaction, a 1,3,5-alkatriene content was 1.32% and an EZ:EE isomer ratio was 89.33:10.67.[Mass spectrum] EI-mass spectrum (70 eV): m/z 226 (M+), 164, 138, 110, 95, 81, 67, 55 Comparative Example 1 Reaction between 4-formyl-(E3)-3-butenyl acetate and alkylidene phosphorane (in the Case where an Alcohol is Protected with an Acetyl Group)Triphenylphosphine (52.51 g, 0.20 mol), n-heptane bromide (3847 g, 0.215 mol) and N,N-dimethylformamide (41.0 g) were placed in a reactor and stirred at 105 to 110° C. for 26 to 30 hours. After stirring, the reaction mixture was cooled to 20° C. and tetrahydrofuran (185.0 g) was added thereto. Then, potassium t-butoxide (21.1 g, 0.188 mol) was added at 10 to 15° C. and the resulting mixture was stirred at 20° C. for one hour. After stirring, the reaction mixture was cooled to -20° C. and 4-formyl-(E3)-3-butenyl acetate (25.87 g, 0.182 mol) was added dropwise thereto at -15 to -5° C.After dropwise addition, the temperature of the mixture was raised to the range of 20 to 25° C. over one hour and the mixture was stirred as it was for one hour. Then, water (100 g) was added to terminate the reaction. The reaction mixture was extracted with toluene (100 g). the organic phase was washed with water and then concentrated under reduced pressure by removing toluene.After concentration, n-hexane (120 g) was added and triphenylphosphine oxide thus precipitated was separated by filtration. The filtrate was concentrated under reduced pressure again and the concentrated solution was distilled under reduced pressure to yield intended (E3,Z5)-3,5-dodecadienyl acetate (9.80 g, 0.04 mol) in a yield of 24.0% and 1,3,5-decatriene (9.87 g, 0.06 mol) in a yield of 33.0%.
	In toluene Reflux;	4.1. General procedure for the synthesis of phosphonium salts (a) General procedure: A mixture of triphenyl phosphine (3 equiv) and the alkyl halide, 1-iodobutane, 1-bromoheptane and 1-bromodecane, respectively, (1 equiv) in toluene was refluxed overnight. The mixture was then allowed to cool and then filtered. The precipitate was washed with cold toluene and dried under vacuo to give the phosphonium salts which were used in the next step without further purification.
	for 48h; Reflux;
33 g	for 5h; Inert atmosphere;	Preparation of L1 intermediate 1 [0036] In a three-necked round-bottomed flask, 23 g (1.1 eq) 1-bromo-n-heptane and 37g (1.0 eq.) triphenylphosphineare added in sequence, purged with nitrogen gas and then heated with stirring for 5 hours. The reaction liquid is filteredby suction, and the filter pad is washed in 200 ml x 3 ethyl acetate and dried to give 33 g white solid 1.
	In acetonitrile

Reference： [1]Pempo, Delphine; Cintrat, Jean-Christophe; Parrain, Jean-Luc; Santelli, Maurice [Tetrahedron, 2000, vol. 56, # 30, p. 5493 - 5497]
[2]Location in patent: experimental part Fiorini, Dennis; Giuli, Sandra; Marcantoni, Enrico; Quassinti, Luana; Bramucci, Massimo; Amantini, Consuelo; Santoni, Giorgio; Buonanno, Federico; Ortenzi, Claudio [Synthesis, 2010, # 9, p. 1550 - 1556]
[3]Hong, Yeonsun; Sengupta, Sandip; Hur, Wooyoung; Sim, Taebo [Journal of Medicinal Chemistry, 2015, vol. 58, # 9, p. 3739 - 3750]
[4]Kumaraswamy, Gullapalli; Jayaprakash, Neerasa [Tetrahedron Letters, 2010, vol. 51, # 50, p. 6500 - 6502]
[5]Pearson; Hutta; Fang [Journal of Organic Chemistry, 2000, vol. 65, # 24, p. 8326 - 8332]
[6]Liu, Jun; Bandyopadhyay, Indrajit; Zheng, Lei; Khdour, Omar M.; Hecht, Sidney M. [ACS Medicinal Chemistry Letters, 2020, vol. 11, # 11, p. 2165 - 2173]
[7]Verduyn, R.; Lagas, R. M.; Dreef, C. E.; Marel, G. A. van der; Boom, J. H. van [Recueil des Travaux Chimiques des Pays-Bas, 1992, vol. 111, # 7/8, p. 367 - 368]
[8]Tyman, John H.P.; Mehet, Satinderjit K. [Chemistry and Physics of Lipids, 2003, vol. 126, # 2, p. 177 - 199]
[9]Location in patent: body text Ragoussis, Valentine; Perdikaris, Stamatis; Karamolegkos, Antonis; Magkiosi, Konstantina [Journal of Agricultural and Food Chemistry, 2008, vol. 56, # 24, p. 11929 - 11932]
[10]Strauss, Marcel A.; Wegner, Hermann A. [Angewandte Chemie - International Edition, 2019, vol. 58, # 51, p. 18552 - 18556][Angew. Chem., 2019, vol. 131, # 51, p. 18724 - 18729,6]
[11]Hauser,C.F. et al. [Journal of Organic Chemistry, 1963, vol. 28, p. 372 - 379]
[12]Dahlhoff, Wilhelm V. [Liebigs Annalen der Chemie, 1992, # 2, p. 109 - 114]
[13]Dobbs, Adrian P.; Venturelli, Alberto; Butler, Laura A.; Parker, Robert J. [Synlett, 2005, # 4, p. 652 - 654]
[14]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD. - US2009/143617, 2009, A1 Location in patent: Page/Page column 3; 4; 4-5
[15]Location in patent: experimental part Veerapen, Natacha; Reddington, Faye; Salio, Mariolina; Cerundolo, Vincenzo; Besra, Gurdyal S. [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 1, p. 221 - 228]
[16]Martín-Rodríguez, Alberto J.; Babarro, Jose M. F.; Lahoz, Fernando; Sansón, Marta; Martín, Víctor S.; Norte, Manuel; Fernández, José J. [PLoS ONE, 2015, vol. 10, # 4]
[17]Current Patent Assignee: HALATION PHOTONICS CORPORATION - EP2894148, 2015, A1 Location in patent: Paragraph 0036
[18]Barker, David; Chhagan, Asha; Park, Kye Chung; Pilkington, Lisa I.; Suckling, David M.; Twidle, Andrew M. [Journal of Agricultural and Food Chemistry, 2020, vol. 68, # 35, p. 9557 - 9567]

5
[ 13423-48-8 ]
[ 67-64-1 ]
[ 2129-95-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: triphenylheptylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane for 0.5h; Inert atmosphere; Stage #2: acetone In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
	(i) NaH, DMSO, (ii) /BRN= 635680/; Multistep reaction;

Reference： [1]Vyvyan, James R.; Brown, Rebecca C.; Woods, Brian P. [Journal of Organic Chemistry, 2009, vol. 74, # 3, p. 1374 - 1376]
[2]Zavada,J. et al. [Collection of Czechoslovak Chemical Communications, 1973, vol. 38, p. 2102 - 2120]

6
[ 4221-03-8 ]
[ 13423-48-8 ]
[ 40642-38-4 ]

Yield	Reaction Conditions	Operation in experiment
47%	With potassium <i>tert</i>-butylate In tetrahydrofuran

Reference： [1]Verduyn, R.; Lagas, R. M.; Dreef, C. E.; Marel, G. A. van der; Boom, J. H. van [Recueil des Travaux Chimiques des Pays-Bas, 1992, vol. 111, # 7/8, p. 367 - 368]

7
[ 56268-03-2 ]
[ 13423-48-8 ]
[ 63408-45-7 ]

Yield	Reaction Conditions	Operation in experiment
63%	With n-butyllithium; 18-crown-6 ether In hexane; toluene
	With sodium amide 1.) benzene, reflux, 8 h, 2.) benzene, RT, 15 h; Multistep reaction;

Reference： [1]Naoshima, Yoshinobu; Kawakubo, Mitsugu; Wakabayashi, Shoji; Hayashi, Shuichi [Agricultural and Biological Chemistry, 1981, vol. 45, # 2, p. 439 - 442]
[2]Yoshida, Takashi; Saito, Shojiro [Bulletin of the Chemical Society of Japan, 1982, vol. 55, # 9, p. 3047 - 3048]

8
[ 56268-03-2 ]
[ 13423-48-8 ]
[ 63408-45-7 ]
[ 63408-51-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium <i>tert</i>-butylate In tetrahydrofuran; dichloromethane at 0℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
	With n-butyllithium 1.) THF, hexane; 2.) THF; Yield given. Multistep reaction. Title compound not separated from byproducts;
	With n-butyllithium 1.) THF, hexane; 2.) THF; Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

Reference： [1]Dasaradhi, Lakkaraju; Rao, Jagadishwar; Bhalerao, Uday T. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 167 - 168]
[2]Sorochinskaya, A. M.; Ishchenko, R. I.; Kovalev, B. G. [Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 237 - 241][Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 2, p. 267 - 272]
[3]Sorochinskaya, A. M.; Ishchenko, R. I.; Kovalev, B. G. [Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 237 - 241][Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 2, p. 267 - 272]

9
[ 56268-03-2 ]
[ 13423-48-8 ]
[ 63408-45-7 ]
[ 791-28-6 ]

Yield	Reaction Conditions	Operation in experiment
60.9%	With sodium hexamethyldisilazane In tetrahydrofuran -78 deg C, 1 h then 25 deg C 12 h;

Reference： [1]Sorochinskaya, A. M.; Kovalev, B. G.; Avdeeva, L. A. [Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, # 2, p. 277 - 283][Zhurnal Organicheskoi Khimii, 1988, vol. 24, # 2, p. 316 - 323]

10
[ 13423-48-8 ]
[ 110720-07-5 ]
(R)-((E)-6-Undec-4-enyl)-tetrahydro-pyran-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium <i>tert</i>-butylate In tetrahydrofuran

Reference： [1]Sakamoto, Akio; Yamamoto, Yukio; Oda, Jun'ichi [Journal of the American Chemical Society, 1987, vol. 109, # 23, p. 7188 - 7189]

11
[ 13423-48-8 ]
[ 77328-83-7 ]
[ 63408-44-6 ]

Yield	Reaction Conditions	Operation in experiment
64%	With n-butyllithium; 18-crown-6 ether In hexane; toluene 1.) 80 deg C - 100 deg C, 1 h, 2.) -35 deg C to -30 deg C, 20 min; -5 deg C to 0 deg C, 1 h; 10 deg C, overnight;
	With sodium amide 1.) benzene, reflux, 8 h, 2.) benzene, RT, 15 h; Yield given. Multistep reaction;

Reference： [1]Naoshima, Yoshinobu; Kawakubo, Mitsugu; Wakabayashi, Shoji; Hayashi, Shuichi [Agricultural and Biological Chemistry, 1981, vol. 45, # 2, p. 439 - 442]
[2]Yoshida, Takashi; Saito, Shojiro [Bulletin of the Chemical Society of Japan, 1982, vol. 55, # 9, p. 3047 - 3048]

12
[ 13423-48-8 ]
[ 77328-83-7 ]
[ 63408-44-6 ]
[ 791-28-6 ]

Yield	Reaction Conditions	Operation in experiment
61%	With hexamethyldisilazide In tetrahydrofuran -78 deg C, 1 h then 25 deg C, 12 h;

Reference： [1]Sorochinskaya, A. M.; Kovalev, B. G.; Avdeeva, L. A. [Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, # 2, p. 277 - 283][Zhurnal Organicheskoi Khimii, 1988, vol. 24, # 2, p. 316 - 323]

13
[ 13423-48-8 ]
[ 139943-71-8 ]
[ 139943-73-0 ]

Yield	Reaction Conditions	Operation in experiment
66%	With sodium amide In tetrahydrofuran at -78℃; for 2h;

Reference： [1]Yadav, J. S.; Upender, Velaparthi; Rao, A. V. Rama [Journal of Organic Chemistry, 1992, vol. 57, # 11, p. 3242 - 3245]

14
[ 13423-48-8 ]
[ 55367-56-1 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h;
	With n-butyllithium In tetrahydrofuran; hexane
	With sodium hexamethyldisilazane In tetrahydrofuran 20 deg C, 20 min, reflux, 1 h;

	With sodium hydride In dimethyl sulfoxide at 20℃; for 1h;
	With potassium <i>tert</i>-butylate In tetrahydrofuran; N,N-dimethyl-formamide at 10 - 20℃; for 1h;	1 Preparation of (E3,Z5)-3,5-dodecadienyl methoxymethyl etherTriphenylphosphine (105.02 g, 0.40 mol), n-heptyl bromide (76.93 g, 0.43 mol) and N,N-dimethylformamide (82.0 g) were placed in a reactor and stirred at 105 to 110° C. for 26 to 30 hours. After stirring, the reaction mixture was cooled to 20° C. and tetrahydrofuran (370.0 g) and potassium t-butoxide (42.10 g, 0.375 mol) were added thereto successively at 10 to 15° C. The resulting mixture was stirred at 20° C. for one hour. After stirring, the reaction mixture was cooled to -20° C. and 4-formyl-(E3)-3-butenyl methoxymethyl ether (52.47 g, 0.364 mol) was added dropwise thereto at -15 to -5° C.After dropwise addition was over, the temperature of the mixture was raised to the range of 20 to 25° C. over one hour and then the mixture was stirred as it was for one hour. Then water (200 g) was added thereto to terminate the reaction. The reaction mixture was extracted with toluene (200 g). The organic phase was washed with water and then concentrated under reduced pressure by removing toluene.After concentration, n-hexane (250 g) was added and triphenylphosphine oxide thus precipitated was separated by filtration. The filtrate was concentrated under reduced pressure again and the concentrate was distilled under reduced pressure to yield intended (E3,Z5)-3,5-dodecadienyl methoxymethyl ether (bp: from 82 to 86° C. [1 mmHg], 52.98 g, 0.23 mol) in a yield of 65.2%.Gas chromatography (DB-5: 30 m×0.25 mm, temperature elevation from 150° C. to 280° C. at a rate of 10° C./min) revealed that as a result of the Wittig reaction, a 1,3,5-alkatriene content was 1.32% and an EZ:EE isomer ratio was 89.33:10.67.[Mass spectrum] EI-mass spectrum (70 eV): m/z 226 (M+), 164, 138, 110, 95, 81, 67, 55 Comparative Example 1 Reaction between 4-formyl-(E3)-3-butenyl acetate and alkylidene phosphorane (in the Case where an Alcohol is Protected with an Acetyl Group)Triphenylphosphine (52.51 g, 0.20 mol), n-heptane bromide (3847 g, 0.215 mol) and N,N-dimethylformamide (41.0 g) were placed in a reactor and stirred at 105 to 110° C. for 26 to 30 hours. After stirring, the reaction mixture was cooled to 20° C. and tetrahydrofuran (185.0 g) was added thereto. Then, potassium t-butoxide (21.1 g, 0.188 mol) was added at 10 to 15° C. and the resulting mixture was stirred at 20° C. for one hour. After stirring, the reaction mixture was cooled to -20° C. and 4-formyl-(E3)-3-butenyl acetate (25.87 g, 0.182 mol) was added dropwise thereto at -15 to -5° C.After dropwise addition, the temperature of the mixture was raised to the range of 20 to 25° C. over one hour and the mixture was stirred as it was for one hour. Then, water (100 g) was added to terminate the reaction. The reaction mixture was extracted with toluene (100 g). the organic phase was washed with water and then concentrated under reduced pressure by removing toluene.After concentration, n-hexane (120 g) was added and triphenylphosphine oxide thus precipitated was separated by filtration. The filtrate was concentrated under reduced pressure again and the concentrated solution was distilled under reduced pressure to yield intended (E3,Z5)-3,5-dodecadienyl acetate (9.80 g, 0.04 mol) in a yield of 24.0% and 1,3,5-decatriene (9.87 g, 0.06 mol) in a yield of 33.0%.
	With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; Inert atmosphere;

Reference： [1]Tolstikov, A. G.; Khakhalina, N. V.; Odinokov, V. N.; Khalilov, L. M.; Spirikhin L. V. [Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 2.1, p. 263 - 268][Zhurnal Organicheskoi Khimii, 1989, vol. 25, # 2, p. 296 - 302]
[2]Clark, Richard S. J.; Holmes, Andrew B.; Matassa, Victor G. [Journal of the Chemical Society. Perkin transactions I, 1990, # 5, p. 1389 - 1400]
[3]Kovalev, B. G.; Sorochinskaya, A. M.; Avdeeva, L. A. [Chemistry of Natural Compounds, 1988, vol. 24, # 1, p. 110 - 112][Khimiya Prirodnykh Soedinenii, 1988, vol. 24, # 1, p. 123 - 126]
[4]Steinreiber, Andreas; Mayer, Sandra F.; Saf, Robert; Faber, Kurt [Tetrahedron Asymmetry, 2001, vol. 12, # 10, p. 1519 - 1528]
[5]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD. - US2009/143617, 2009, A1 Location in patent: Page/Page column 3; 4; 4-5
[6]Reiter, Dominik; Frisch, Philipp; Szilvási, Tibor; Inoue, Shigeyoshi [Journal of the American Chemical Society, 2019, vol. 141, # 42, p. 16991 - 16996]

15
[ 13423-48-8 ]
[ 121-33-5 ]
[ 140136-22-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium carbonate In water; isopropyl alcohol at 60℃; for 6h;

Reference： [1]Bettach; Le Bigot; Mouloungui; Delmas; Gaset [Synthetic Communications, 1992, vol. 22, # 4, p. 513 - 518]

16
[ 13423-48-8 ]
[ 15186-48-8 ]
[ 252009-65-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	With n-butyllithium In tetrahydrofuran at -78℃;
82%	Stage #1: triphenylheptylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 0.166667h; Stage #2: 2,3-isopropylidene-glyceraldehyde In tetrahydrofuran; hexane at -10 - 0℃; for 2h;

Reference： [1]Coxon, Geoffrey D.; Knobl, Stefan; Roberts, Evan; Baird, Mark S.; Al Dulayymi, Juma R.; Besra, Gurdyal S.; Brennan, Patrick J.; Minnikin, David E. [Tetrahedron Letters, 1999, vol. 40, # 36, p. 6689 - 6692]
[2]Coxon, Geoffrey D.; Al-Dulayymi, Juma R.; Baird, Mark S.; Knobl, Stefan; Roberts, Evan; Minnikin, David E. [Tetrahedron Asymmetry, 2003, vol. 14, # 9, p. 1211 - 1222]

17
[ 13423-48-8 ]
[ 116370-28-6 ]
(S,Z)-3-methyltridec-6-en-1-ol [ No CAS ]
(S,E)-3-methyltridec-6-en-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium In tetrahydrofuran; hexane at -80 - 20℃; Title compound not separated from byproducts;

Reference： [1]Pempo, Delphine; Cintrat, Jean-Christophe; Parrain, Jean-Luc; Santelli, Maurice [Tetrahedron, 2000, vol. 56, # 30, p. 5493 - 5497]

18
[ 13423-48-8 ]
[ 303053-01-2 ]
(2R,2'R,5'S)-((Z)-5'-Undec-4-enyl)-tetrahydro-[2,2']bifuranyl-5-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: triphenylheptylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Stage #2: (4R,5R,8R)-5,8-oxido-12-oxotricosan-1,4-olide In tetrahydrofuran; hexane for 0.5h; Further stages.;

Reference： [1]Avedissian, Hovsep; Sinna, Santosh C.; Yazbak, Ahmad; Sinha, Anjana; Neogi, Partha; Sinha, Subhash C.; Keinan, Ehud [Journal of Organic Chemistry, 2000, vol. 65, # 19, p. 6035 - 6051]

19
[ 13423-48-8 ]
[ 264146-46-5 ]
[ 264146-47-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium <i>tert</i>-butylate In 1,4-dioxane at 20℃; for 1h;

Reference： [1]Hadfield, John A.; McGown, Alan T.; Butler, John [Molecules, 2000, vol. 5, # 1, p. 82 - 88]

20
[ 13423-48-8 ]
[ 444884-35-9 ]
[ 221367-95-9 ]

Yield	Reaction Conditions	Operation in experiment
77%	Stage #1: triphenylheptylphosphonium bromide With sodium hexamethyldisilazane In toluene at 20℃; for 1h; Stage #2: 3-((4R,5R)-5-{(R)-3-[(2R,5R)-5-((R)-2,2-Dimethyl-[1,3]dioxepan-4-yl)-tetrahydro-furan-2-yl]-3-iodo-propyl}-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionaldehyde In toluene at -78 - 20℃;

Reference： [1]Dabideen, Darrin; Ruan, Zheming; Mootoo, David R [Tetrahedron, 2002, vol. 58, # 11, p. 2077 - 2084]

21
[ 13423-48-8 ]
(2R,5S,6R)-1-Benzhydryl-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-piperidine-2-carbaldehyde [ No CAS ]
(2R,3S,6R)-1-Benzhydryl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-((Z)-oct-1-enyl)-piperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With potassium hexamethylsilazane In tetrahydrofuran; toluene

Reference： [1]Bailey, Patrick D; Smith, Peter D; Morgan, Keith M; Rosair, Georgina M [Tetrahedron Letters, 2002, vol. 43, # 6, p. 1071 - 1074]

22
[ 13423-48-8 ]
[ 444808-97-3 ]
[ 444808-98-4 ]

Yield	Reaction Conditions	Operation in experiment
46%	With n-butyllithium In tetrahydrofuran; hexane at -50℃; for 0.666667h;

Reference： [1]Compostella, Federica; Colombo, Diego; Ferraboschi, Patrizia; Scala, Antonio; Toma, Lucio; Ronchetti, Fiamma [European Journal of Organic Chemistry, 2002, # 8, p. 1429 - 1435]

23
[ 13423-48-8 ]
[ 100-83-4 ]
[ 702660-60-4 ]

Yield	Reaction Conditions	Operation in experiment
52.3%	Stage #1: triphenylheptylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane Stage #2: meta-hydroxybenzaldehyde In tetrahydrofuran; hexane

Reference： [1]Tyman, John H.P.; Mehet, Satinderjit K. [Chemistry and Physics of Lipids, 2003, vol. 126, # 2, p. 177 - 199]

24
[ 427901-54-0 ]
[ 13423-48-8 ]
[ 851316-93-3 ]

Yield	Reaction Conditions	Operation in experiment
68%	Stage #1: triphenylheptylphosphonium bromide With n-butyllithium In tetrahydrofuran Stage #2: acetic acid 15-oxo-pentadecyl ester In tetrahydrofuran

Reference： [1]Dobbs, Adrian P.; Venturelli, Alberto; Butler, Laura A.; Parker, Robert J. [Synlett, 2005, # 4, p. 652 - 654]

25
[ 13423-48-8 ]
[ 117948-96-6 ]
[ 849355-65-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	With 0,2,4-dichlorophenyl-0-methylisopropylamidothiophosphate; sodium amide In tetrahydrofuran at -78 - 20℃;

Reference： [1]Ghomsi, Joseph-Nathan Téné; Goureau, Olivine; Treilhou, Michel [Tetrahedron Letters, 2005, vol. 46, # 9, p. 1537 - 1539]

26
[ 13423-48-8 ]
[ 1122-91-4 ]
[ 876391-67-2 ]

Yield	Reaction Conditions	Operation in experiment
57%	Stage #1: triphenylheptylphosphonium bromide; 4-bromo-benzaldehyde With n-butyllithium In tetrahydrofuran Stage #2: With n-butyllithium In tetrahydrofuran; N,N-dimethyl-formamide

Reference： [1]Lu, Xuequan; Bittman, Robert [Tetrahedron Letters, 2006, vol. 47, # 5, p. 825 - 827]

27
[ 1191-30-6 ]
[ 13423-48-8 ]
[ 146955-48-8 ]

Yield	Reaction Conditions	Operation in experiment
10%	Stage #1: triphenylheptylphosphonium bromide With n-butyllithium In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 5-bromopentanal In tetrahydrofuran at 20℃; Further stages.;

Reference： [1]Pearson; Hutta; Fang [Journal of Organic Chemistry, 2000, vol. 65, # 24, p. 8326 - 8332]

28
5,5-dimethyl-2-oxo-3-methyl-5,6-dihydro-2H-pyran-4-carboxyaldehyde [ No CAS ]
[ 13423-48-8 ]
3,5,5-trimethyl-4-oct-1-enyl-5,6-dihydro-2H-pyran-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	Stage #1: triphenylheptylphosphonium bromide With n-butyllithium In tetrahydrofuran at -10℃; for 0.5h; Stage #2: 5,5-dimethyl-2-oxo-3-methyl-5,6-dihydro-2H-pyran-4-carboxyaldehyde In tetrahydrofuran at -10℃; for 3h;

Reference： [1]Cateni, Francesca; Zilic, Jelena; Zacchigna, Marina; Bonivento, Paolo; Frausin, Fabiana; Scarcia, Vito [European Journal of Medicinal Chemistry, 2006, vol. 41, # 2, p. 192 - 200]

29
3-[(2S,3R,6S)-6-[(S)-1-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-propyl]-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-propionaldehyde [ No CAS ]
[ 13423-48-8 ]
[ 910057-88-4 ]

Yield	Reaction Conditions	Operation in experiment
125 mg	With sodium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; for 3.5h;

Reference： [1]Bandur, Nina G.; Brueckner, David; Hoffmann, Reinhard W.; Koert, Ulrich [Organic Letters, 2006, vol. 8, # 17, p. 3829 - 3831]

30
[ 36938-28-0 ]
[ 13423-48-8 ]
5,6-Dimethoxy-4-((E)-oct-1-enyl)-benzo[1,3]dioxole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: triphenylheptylphosphonium bromide With n-butyllithium In tetrahydrofuran at 0℃; Stage #2: 5,6-dimethoxy-benzo[1,3]dioxole-4-carbaldehyde In tetrahydrofuran for 0.166667h;

Reference： [1]Chen, Jianyong; Nikolovska-Coleska, Zaneta; Wang, Guoping; Qiu, Su; Wang, Shaomeng [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 22, p. 5805 - 5808]

31
[ 13423-48-8 ]
[ 158937-15-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: triphenylheptylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 0.25h; Further stages.;

Reference： [1]Shin, Hyunshun; Gennadios, Heather A.; Whittington, Douglas A.; Christianson, David W. [Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 7, p. 2617 - 2623]

32
[ 13423-48-8 ]
[ 123367-67-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C 2: 62 percent / tetrahydrofuran / 1 h / -78 °C 3: 99 percent / H₂ / 5percent Pd-C / ethanol / 20 °C / 3040 Torr

Reference： [1]Tolstikov, A. G.; Khakhalina, N. V.; Odinokov, V. N.; Khalilov, L. M.; Spirikhin L. V. [Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 2.1, p. 263 - 268][Zhurnal Organicheskoi Khimii, 1989, vol. 25, # 2, p. 296 - 302]

33
[ 13423-48-8 ]
[ 916320-34-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-BuLi / tetrahydrofuran / 0 °C 1.2: tetrahydrofuran / 0.17 h 2.1: H₂ / Pd/C / ethyl acetate / 20 °C 3.1: ceric ammonium nitrate / acetonitrile; H₂O / 1 h / 0 °C

Reference： [1]Chen, Jianyong; Nikolovska-Coleska, Zaneta; Wang, Guoping; Qiu, Su; Wang, Shaomeng [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 22, p. 5805 - 5808]

34
[ 13423-48-8 ]
[ 916320-28-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: n-BuLi / tetrahydrofuran / 0 °C 1.2: tetrahydrofuran / 0.17 h 2.1: H₂ / Pd/C / ethyl acetate / 20 °C

Reference： [1]Chen, Jianyong; Nikolovska-Coleska, Zaneta; Wang, Guoping; Qiu, Su; Wang, Shaomeng [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 22, p. 5805 - 5808]

35
[ 13423-48-8 ]
[ 21182-47-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: n-BuLi / tetrahydrofuran / 0 °C 1.2: tetrahydrofuran / 0.17 h 2.1: H₂ / Pd/C / ethyl acetate / 20 °C 3.1: ceric ammonium nitrate / acetonitrile; H₂O / 1 h / 0 °C 4.1: perchloric acid; aq. HCl / dioxane / 48 h / 20 °C

Reference： [1]Chen, Jianyong; Nikolovska-Coleska, Zaneta; Wang, Guoping; Qiu, Su; Wang, Shaomeng [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 22, p. 5805 - 5808]

36
[ 13423-48-8 ]
[ 402616-23-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1.1: n-BuLi / tetrahydrofuran 1.2: 57 percent / n-BuLi / tetrahydrofuran; dimethylformamide 2.1: n-BuLi / tetrahydrofuran 2.2: 81 percent / H₂ / Pd(OH)2/C / methanol 3.1: PCC; NaOAc; molecular sieves / CH₂Cl₂ 3.2: 76 percent / Et₃N / CH₂Cl₂ 4.1: 87 percent / NaBH₄ / CeCl₃ / methanol 5.1: 83 percent / (+)-DIPT; cumene hydroperoxide; MS / Ti(OPr-i)4 / CH₂Cl₂ / -20 °C 6.1: DBU / CH₂Cl₂ / 1.5 h / 0 °C 6.2: 74 percent / Et₂AlCl / CH₂Cl₂ / 0 - 20 °C 7.1: 1H-tetrazole / CH₂Cl₂; acetonitrile / 6 h 7.2: 78 percent / t-BuOOH / 20 °C 8.1: 81 percent / aq. HCl / tetrahydrofuran / 20 °C

Reference： [1]Lu, Xuequan; Bittman, Robert [Tetrahedron Letters, 2006, vol. 47, # 5, p. 825 - 827]

37
[ 13423-48-8 ]
[ 402616-26-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1.1: n-BuLi / tetrahydrofuran 1.2: 57 percent / n-BuLi / tetrahydrofuran; dimethylformamide 2.1: n-BuLi / tetrahydrofuran 2.2: 81 percent / H₂ / Pd(OH)2/C / methanol 3.1: PCC; NaOAc; molecular sieves / CH₂Cl₂ 3.2: 76 percent / Et₃N / CH₂Cl₂ 4.1: 87 percent / NaBH₄ / CeCl₃ / methanol 5.1: 83 percent / (-)-DIPT; cumene hydroperoxide; MS / Ti(OPr-i)4 / CH₂Cl₂ / -20 °C 6.1: DBU / CH₂Cl₂ / 1.5 h / 0 °C 6.2: Et₂AlCl / CH₂Cl₂ / 0 - 20 °C 7.1: 1H-tetrazole / CH₂Cl₂; acetonitrile 7.2: t-BuOOH / 20 °C 8.1: aq. HCl / tetrahydrofuran / 20 °C

Reference： [1]Lu, Xuequan; Bittman, Robert [Tetrahedron Letters, 2006, vol. 47, # 5, p. 825 - 827]

38
[ 13423-48-8 ]
[ 876391-69-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: n-BuLi / tetrahydrofuran 1.2: 57 percent / n-BuLi / tetrahydrofuran; dimethylformamide 2.1: n-BuLi / tetrahydrofuran 2.2: 81 percent / H₂ / Pd(OH)2/C / methanol 3.1: PCC; NaOAc; molecular sieves / CH₂Cl₂ 3.2: 76 percent / Et₃N / CH₂Cl₂ 4.1: 87 percent / NaBH₄ / CeCl₃ / methanol

Reference： [1]Lu, Xuequan; Bittman, Robert [Tetrahedron Letters, 2006, vol. 47, # 5, p. 825 - 827]

39
[ 13423-48-8 ]
[ 876391-70-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: n-BuLi / tetrahydrofuran 1.2: 57 percent / n-BuLi / tetrahydrofuran; dimethylformamide 2.1: n-BuLi / tetrahydrofuran 2.2: 81 percent / H₂ / Pd(OH)2/C / methanol 3.1: PCC; NaOAc; molecular sieves / CH₂Cl₂ 3.2: 76 percent / Et₃N / CH₂Cl₂ 4.1: 87 percent / NaBH₄ / CeCl₃ / methanol 5.1: 83 percent / (+)-DIPT; cumene hydroperoxide; MS / Ti(OPr-i)4 / CH₂Cl₂ / -20 °C

Reference： [1]Lu, Xuequan; Bittman, Robert [Tetrahedron Letters, 2006, vol. 47, # 5, p. 825 - 827]

40
[ 13423-48-8 ]
[ 876391-74-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: n-BuLi / tetrahydrofuran 1.2: 57 percent / n-BuLi / tetrahydrofuran; dimethylformamide 2.1: n-BuLi / tetrahydrofuran 2.2: 81 percent / H₂ / Pd(OH)2/C / methanol 3.1: PCC; NaOAc; molecular sieves / CH₂Cl₂ 3.2: 76 percent / Et₃N / CH₂Cl₂ 4.1: 87 percent / NaBH₄ / CeCl₃ / methanol 5.1: 83 percent / (-)-DIPT; cumene hydroperoxide; MS / Ti(OPr-i)4 / CH₂Cl₂ / -20 °C

Reference： [1]Lu, Xuequan; Bittman, Robert [Tetrahedron Letters, 2006, vol. 47, # 5, p. 825 - 827]

41
[ 13423-48-8 ]
[ 876391-72-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: n-BuLi / tetrahydrofuran 1.2: 57 percent / n-BuLi / tetrahydrofuran; dimethylformamide 2.1: n-BuLi / tetrahydrofuran 2.2: 81 percent / H₂ / Pd(OH)2/C / methanol 3.1: PCC; NaOAc; molecular sieves / CH₂Cl₂ 3.2: 76 percent / Et₃N / CH₂Cl₂ 4.1: 87 percent / NaBH₄ / CeCl₃ / methanol 5.1: 83 percent / (+)-DIPT; cumene hydroperoxide; MS / Ti(OPr-i)4 / CH₂Cl₂ / -20 °C 6.1: DBU / CH₂Cl₂ / 1.5 h / 0 °C 6.2: 74 percent / Et₂AlCl / CH₂Cl₂ / 0 - 20 °C

Reference： [1]Lu, Xuequan; Bittman, Robert [Tetrahedron Letters, 2006, vol. 47, # 5, p. 825 - 827]

42
[ 13423-48-8 ]
[ 876391-75-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: n-BuLi / tetrahydrofuran 1.2: 57 percent / n-BuLi / tetrahydrofuran; dimethylformamide 2.1: n-BuLi / tetrahydrofuran 2.2: 81 percent / H₂ / Pd(OH)2/C / methanol 3.1: PCC; NaOAc; molecular sieves / CH₂Cl₂ 3.2: 76 percent / Et₃N / CH₂Cl₂ 4.1: 87 percent / NaBH₄ / CeCl₃ / methanol 5.1: 83 percent / (-)-DIPT; cumene hydroperoxide; MS / Ti(OPr-i)4 / CH₂Cl₂ / -20 °C 6.1: DBU / CH₂Cl₂ / 1.5 h / 0 °C 6.2: Et₂AlCl / CH₂Cl₂ / 0 - 20 °C

Reference： [1]Lu, Xuequan; Bittman, Robert [Tetrahedron Letters, 2006, vol. 47, # 5, p. 825 - 827]

43
[ 13423-48-8 ]
phosphoric acid di-<i>tert</i>-butyl ester 4-[2-(4-octyl-phenyl)-ethyl]-2-trichloromethyl-4,5-dihydro-oxazol-4-ylmethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: n-BuLi / tetrahydrofuran 1.2: 57 percent / n-BuLi / tetrahydrofuran; dimethylformamide 2.1: n-BuLi / tetrahydrofuran 2.2: 81 percent / H₂ / Pd(OH)2/C / methanol 3.1: PCC; NaOAc; molecular sieves / CH₂Cl₂ 3.2: 76 percent / Et₃N / CH₂Cl₂ 4.1: 87 percent / NaBH₄ / CeCl₃ / methanol 5.1: 83 percent / (-)-DIPT; cumene hydroperoxide; MS / Ti(OPr-i)4 / CH₂Cl₂ / -20 °C 6.1: DBU / CH₂Cl₂ / 1.5 h / 0 °C 6.2: Et₂AlCl / CH₂Cl₂ / 0 - 20 °C 7.1: 1H-tetrazole / CH₂Cl₂; acetonitrile 7.2: t-BuOOH / 20 °C

Reference： [1]Lu, Xuequan; Bittman, Robert [Tetrahedron Letters, 2006, vol. 47, # 5, p. 825 - 827]

44
[ 13423-48-8 ]
[ 876391-73-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: n-BuLi / tetrahydrofuran 1.2: 57 percent / n-BuLi / tetrahydrofuran; dimethylformamide 2.1: n-BuLi / tetrahydrofuran 2.2: 81 percent / H₂ / Pd(OH)2/C / methanol 3.1: PCC; NaOAc; molecular sieves / CH₂Cl₂ 3.2: 76 percent / Et₃N / CH₂Cl₂ 4.1: 87 percent / NaBH₄ / CeCl₃ / methanol 5.1: 83 percent / (+)-DIPT; cumene hydroperoxide; MS / Ti(OPr-i)4 / CH₂Cl₂ / -20 °C 6.1: DBU / CH₂Cl₂ / 1.5 h / 0 °C 6.2: 74 percent / Et₂AlCl / CH₂Cl₂ / 0 - 20 °C 7.1: 1H-tetrazole / CH₂Cl₂; acetonitrile / 6 h 7.2: 78 percent / t-BuOOH / 20 °C

Reference： [1]Lu, Xuequan; Bittman, Robert [Tetrahedron Letters, 2006, vol. 47, # 5, p. 825 - 827]

45
[ 13423-48-8 ]
[ 20056-69-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane 1.2: 52.3 percent / tetrahydrofuran; hexane 2.1: 43 percent / H₂ / Pd/C / ethanol / 20 °C / ambient pressure

Reference： [1]Tyman, John H.P.; Mehet, Satinderjit K. [Chemistry and Physics of Lipids, 2003, vol. 126, # 2, p. 177 - 199]

46
[ 13423-48-8 ]
[ 702660-66-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane 1.2: 52.3 percent / tetrahydrofuran; hexane 2.1: 43 percent / H₂ / Pd/C / ethanol / 20 °C / ambient pressure 3.1: ethylmagnesium bromide / diethyl ether / 16 h / 20 °C 3.2: 53.6 percent / hexamethylphosphoramide / benzene / Heating

Reference： [1]Tyman, John H.P.; Mehet, Satinderjit K. [Chemistry and Physics of Lipids, 2003, vol. 126, # 2, p. 177 - 199]

47
[ 13423-48-8 ]
2-hydroxymethyl-5-n-octylphenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane 1.2: 52.3 percent / tetrahydrofuran; hexane 2.1: 43 percent / H₂ / Pd/C / ethanol / 20 °C / ambient pressure 3.1: ethylmagnesium bromide / diethyl ether / 16 h / 20 °C 3.2: 53.6 percent / hexamethylphosphoramide / benzene / Heating 4.1: 53.2 percent / sodium borohydride / methanol / 16 h / 0 - 20 °C

Reference： [1]Tyman, John H.P.; Mehet, Satinderjit K. [Chemistry and Physics of Lipids, 2003, vol. 126, # 2, p. 177 - 199]

48
[ 13423-48-8 ]
[ 566928-15-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-BuLi / hexane; tetrahydrofuran / 0.17 h / -78 - 20 °C 1.2: 82 percent / hexane; tetrahydrofuran / 2 h / -10 - 0 °C 2.1: 90 percent / Et₂Zn / 1,2-dichloro-ethane / -30 - 0 °C 3.1: 80 percent / aq. HCl / methanol / 2 h / 20 °C
	Multi-step reaction with 3 steps 1: 82 percent / n-BuLi / tetrahydrofuran / -78 °C 2: 90 percent / Et₂Zn / 1,2-dichloro-ethane / -30 °C 3: 80 percent / HCl / methanol

Reference： [1]Coxon, Geoffrey D.; Al-Dulayymi, Juma R.; Baird, Mark S.; Knobl, Stefan; Roberts, Evan; Minnikin, David E. [Tetrahedron Asymmetry, 2003, vol. 14, # 9, p. 1211 - 1222]
[2]Coxon, Geoffrey D.; Knobl, Stefan; Roberts, Evan; Baird, Mark S.; Al Dulayymi, Juma R.; Besra, Gurdyal S.; Brennan, Patrick J.; Minnikin, David E. [Tetrahedron Letters, 1999, vol. 40, # 36, p. 6689 - 6692]

49
[ 13423-48-8 ]
2-O-(6,7,8,9,10,11,12,13-octadeoxy-β-D-galacto-tridecopyranosyl)glycerol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 46 percent / BuLi / hexane; tetrahydrofuran / 0.67 h / -50 °C 2: 100 percent / AcOH; H₂ / Pd/C / methanol / 72 h

Reference： [1]Compostella, Federica; Colombo, Diego; Ferraboschi, Patrizia; Scala, Antonio; Toma, Lucio; Ronchetti, Fiamma [European Journal of Organic Chemistry, 2002, # 8, p. 1429 - 1435]

50
[ 13423-48-8 ]
[ 19368-92-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) NaCH₂SOMe / 1.) DMSO, 60 deg, 30 min, 2.) DMSO, 50 deg C, overnight 2: H₂ / PtO₂ / ethyl acetate / 1 h

Reference： [1]Jinno, Shuji; Okita, Takaaki [Chemical and Pharmaceutical Bulletin, 1998, vol. 46, # 11, p. 1688 - 1694]

51
[ 13423-48-8 ]
4-Octyl-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) KOC(CH₃)3, 2.) 6 N HCl / 1.) THF, 2.) acetone, reflux 2: H₂ / 5percent Pd/C / methanol

Reference： [1]Stark; Ligneau; Arrang; Schwartz; Schunack [Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 15, p. 2011 - 2016]

52
[ 13423-48-8 ]
[ 100668-23-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) NaH, DMSO / 1.) 70-80 deg C, 15 min, then room t., 20 min, 2.) DMSO, room t., 1.5 h 2: 54 percent / pTs-OH / methanol / 2 h / 0 °C

Reference： [1]Sugiura; Naito; Yamaura; Fukaya; Yokoyama [Chemical and Pharmaceutical Bulletin, 1989, vol. 37, # 4, p. 1039 - 1043]

53
[ 13423-48-8 ]
[ 142563-10-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 1.) n-BuLi / 1.) THF, n-hexane, 0 deg C, 1 h, 2.) THF, rt, overnight 2: 74 percent / pyridine / Ambient temperature 3: 88 percent / NaH / tetrahydrofuran / Ambient temperature 4: 1.) lithium hexamethyldisilazide / 1.) THF, 0 deg C to rt, 1 h, 2.) THF, rt, overnight 5: 2.1 g / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / Ambient temperature 6: 73 percent / H₂ / Raney nickel / ethanol / Heating

Reference： [1]Ebata, Takashi; Kawakami, Hiroshi; Koseki, Koshi; Matsumoto, Katsuya; Matsushita, Hajime [Bioscience, Biotechnology and Biochemistry, 1992, vol. 56, # 5, p. 818 - 819]

54
[ 13423-48-8 ]
[ 130890-39-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: nBuLi / THF, r.t. 2: H₂ / 10percent Pd/C / ethanol / 6 h / 760 Torr / Ambient temperature 3: 80 percent / Amberlite IR 120 H+ / 12 h / 80 °C 4: 80 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature 5: DDQ / CH₂Cl₂; H₂O / 1 h / Ambient temperature

Reference： [1]Sharma; Vepachedu [Tetrahedron Letters, 1990, vol. 31, # 34, p. 4931 - 4932]

55
[ 13423-48-8 ]
[ 130890-37-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: nBuLi / THF, r.t. 2: H₂ / 10percent Pd/C / ethanol / 6 h / 760 Torr / Ambient temperature 3: 80 percent / Amberlite IR 120 H+ / 12 h / 80 °C

Reference： [1]Sharma; Vepachedu [Tetrahedron Letters, 1990, vol. 31, # 34, p. 4931 - 4932]

56
[ 13423-48-8 ]
[ 130890-36-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: nBuLi / THF, r.t. 2: H₂ / 10percent Pd/C / ethanol / 6 h / 760 Torr / Ambient temperature

Reference： [1]Sharma; Vepachedu [Tetrahedron Letters, 1990, vol. 31, # 34, p. 4931 - 4932]

57
[ 13423-48-8 ]
[ 130890-38-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: nBuLi / THF, r.t. 2: H₂ / 10percent Pd/C / ethanol / 6 h / 760 Torr / Ambient temperature 3: 80 percent / Amberlite IR 120 H+ / 12 h / 80 °C 4: 80 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature

Reference： [1]Sharma; Vepachedu [Tetrahedron Letters, 1990, vol. 31, # 34, p. 4931 - 4932]

58
[ 13423-48-8 ]
[ 41497-46-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: butyl-lithium / tetrahydrofuran; hexane 2: 87 percent / tetrahydrofuran / 12 h / Heating 3: 83 percent / H₂ / 5percent Pd/C / ethyl acetate; methanol / 24 h / Ambient temperature

Reference： [1]Clark, Richard S. J.; Holmes, Andrew B.; Matassa, Victor G. [Journal of the Chemical Society. Perkin transactions I, 1990, # 5, p. 1389 - 1400]

59
[ 29786-93-4 ]
2-(4-iodophenyl)-2-nonene [ No CAS ]
[ 13329-40-3 ]
ammonium chloride [ No CAS ]
[ 13423-48-8 ]
2-(4-iodophenyl)nonane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
11.45 g (91%)	With triethylsilane; trifluoroacetic acid In tetrahydrofuran; hexane; water; ethyl acetate	9 2-(4-Iodophenyl)nonane STR12 EXAMPLE 9 2-(4-Iodophenyl)nonane STR12 A suspension of 30.09 g (68.2 mmol) of N-heptyl-triphenylphosphonium bromide in 68 ml of dry THF was placed under nitrogen. The suspension was cooled to 0° C. and a 2.38 M solution of n-Buli in hexane (27.7 ml, 65.9 mmol) was added dropwise via syringe. The resulting deep red solution was stirred 30 min. at 0° C. before a solution of 12.00 g (45.5 mmol) of 4-iodoacetophenone in 45 ml of dry THF was added dropwise. The resulting solution was allowed to warm to room temperature at which time an orange suspension formed. The suspension was stirred at room temperature for 72 hrs and was cooled to 0° C. A solution of saturated NH4 Cl in water was added dropwise until the suspension was colorless. The mixture was partitioned between 300 ml of water and 250 ml of ethyl acetate. The ethyl acetate layer was then washed with brine (50 ml), dried over Na2 SO4 and concentrated in vacuo to yield an oily tan solid. The solid was washed with hexane (200 ml), filtered and the filtrate was concentrated in vacuo to yield 12.26 g of yellow oil. The oil was purified by flash chromatography on 367 g of silica gel with 2.5% ethyl acetate/hexane as eluent. The first 525 ml to elute contained nothing while the pure product eluted with the next 500 ml. Concentration in vacuo afforded 9.98 g (67%) of product isomers as a slightly yellow tinted oil. 1 H-NMR (300 MHz) spectral data were consistent with the desired structure. A mixture of 12.50 g (38.08 mmol) of 2-(4-iodophenyl)-2-nonene and 6.42 g (55.2 mmol) of triethylsilane was cooled to 0° C. Trifluoroacetic acid (13.03 g, 114.2 mmol) was added dropwise and the resulting mixture was stirred at room temperature for 22 hrs before it was heated to reflux for 30 min. The mixture was cooled and partitioned between 200 ml hexanes and 100 ml of 10% K2 CO3 in water. The hexane layer was washed with brine (50 ml) and dried over Na2 SO4. The colorless solution was concentrated in vacuo to 12.31 g of a colorless oil The oil was purified by flash chromatography on 370 g of silica gel with hexane as the eluent. Concentration in vacuo afforded 11.45 g (91%) of product as a mobile colorless oil. Title Compound: 1 H (300 MHz) and 13 C (75 MHz) NMR spectra were consistent with the desired structure. FAB/MS: M+330. Calculated for C15 H23 I: C, 54.55; H, 7.02. Found: C, 55.00, H, 7.02.
11.45 g (91%)	With triethylsilane; trifluoroacetic acid In tetrahydrofuran; hexane; water; ethyl acetate	9 2-(4-Iodophenyl)nonane STR12 EXAMPLE 9 2-(4-Iodophenyl)nonane STR12 A suspension of 30.09 g (68.2 mmol) of N-heptyl-triphenylphosphonium bromide in 68 ml of dry THF was placed under nitrogen. The suspension was cooled to 0° C. and a 2.38M solution of n-Buli in hexane (27.7 ml, 65.9 mmol) was added dropwise via syringe. The resulting deep red solution was stirred 30 min. at 0° C. before a solution of 12.00 g (45.5 mmol) of 4-iodoacetophenone in 45 ml of dry THF was added dropwise. The resulting solution was allowed to warm to room temperature at which time an orange suspension formed. The suspension was stirred at room temperature for 72 hrs and was cooled to 0° C. A solution of saturated NH4 Cl in water was added dropwise until the suspension was colorless. The mixture was partitioned between 300 ml of water and 250 ml of ethyl acetate. The ethyl acetate layer was then washed with brine (50 ml), dried over Na2 SO4 and concentrated in vacuo to yield an oily tan solid. The solid was washed with hexane (200 ml), filtered and the filtrate was concentrated in vacuo to yield 12.26 g of yellow oil. The oil was purified by flash chromatography on 367 g of silica gel with 2.5% ethyl acetate/hexane as eluent. The first 525 ml to elute contained nothing while the pure product eluted with the next 500 ml. Concentration in vacuo afforded 9.98 g (67%) of product isomers as a slightly yellow tinted oil. 1 H-NMR (300 MHz) spectral data were consistent with the desired structure. A mixture of 12.50 g (38.08 mmol) of 2-(4-iodophenyl)-2-nonene and 6.42 g (55.2 mmol) of triethylsilane was cooled to 0° C. Trifluoroacetic acid (13.03 g, 114.2 mmol) was added dropwise and the resulting mixture was stirred at room temperature for 22 hrs before it was heated to reflux for 30 min. The mixture was cooled and partitioned between 200 ml hexanes and 100 ml of 10% K2 CO3 in water. The hexane layer was washed with brine (50 ml) and dried over Na2 SO4. The colorless solution was concentrated in vacuo to 12.31 g of a colorless oil The oil was purified by flash chromatography on 370 g of silica gel with hexane as the eluent. Concentration in vacuo afforded 11.45 g (91%) of product as a mobile colorless oil. Title Compound 1 H (300 MHz) and 13 C (75 MHz) NMR spectra were consistent with the desired structure. FAB/MS: M+330. Calculated for C15 H23 I: C, 54.55; H, 7.02. Found: C, 55.00, H, 7.02.

Reference： [1]Current Patent Assignee: GENERAL ELECTRIC CO - US5308607, 1994, A
[2]Current Patent Assignee: GENERAL ELECTRIC CO - US5334370, 1994, A

60
[ 157360-48-0 ]
[ 13423-48-8 ]
5-benzyloxy-4-tert-butyl-2-(1-octenyl)benzofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With n-butyllithium; sodium bicarbonate In tetrahydrofuran; water; pentane	R.5 Synthesis of 5-Benzyloxy-4-tert-Butyl-2-(1-octenyl)benzofuran Reference Example 5 Synthesis of 5-Benzyloxy-4-tert-Butyl-2-(1-octenyl)benzofuran A pentane solution (2.6 ml, 4.2 mmol) of 1.6M n-butyllithium was added dropwise to a solution of n-heptyltriphenylphosphonium bromide (1.84 g, 4.2 mmol) in tetrahydrofuran (10 ml) under a nitrogen atmosphere. After stirring the mixture at room temperature for 30 min, a solution of 5-benzyloxy-4-tert-butyl-2-formylbenzofuran (1.0 g, 3.2 mmol) in tetrahydrofuran (10 ml) was added dropwise. Subsequently, the mixture was stirred at room temperature for 30 min, poured into ice water and subjected to extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and water, then dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (chloroform) to afford 5-benzyloxy-4-tert-butyl-2-(1-octenyl)benzofuran [1.14 g (yield, 91%)]. Mass 392(M+), 301, 277, 167, 91, 57 1 H NMR (60 MHz, CDCl3) δ ppm 0.89(t,3H), 1.13-1.72(m,8H), 1.56(s,9H), 1.93-2.62(m,2H), 5.03(s,2H), 6.02-6.40(m,2H), 6.78-7.46(m,8H)

Reference： [1]Current Patent Assignee: Chugai Pharmaceutical (in: Roche); ROCHE HOLDING AG - US5574178, 1996, A

61
5-acetoxy-4,6-di-tert-butyl-2-formylbenzofuran [ No CAS ]
[ 13423-48-8 ]
5-acetoxy-4,6-di-tert-butyl-2-(1-octenyl)benzofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With n-butyllithium; ammonium chloride In tetrahydrofuran; hexane; ethyl acetate; pentane	25.2 2) 2) Synthesis of 5-Acetoxy-4,6-Di-tert-Butyl-2-(1-Octenyl)benzofuran A pentane solution (6.0 ml) of 1.6M n-butyllithium was added dropwise to a solution of n-heptyltriphenylphosphonium bromide (4.2 g) in tetrahydrofuran (30 ml) under a nitrogen atmosphere. After stirring the mixture at room temperature for 90 min, a solution of 5-acetoxy-4,6-di-tert-butyl-2-formylbenzofuran (2.54 g) in tetrahydrofuran (20 ml) was added dropwise. Subsequently, the mixture was heated under reflux for 1 h and, after cooling, a saturated aqueous solution of ammonium chloride was added and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane) to afford 5-acetoxy-4,6-di-tert-butyl-2-(1-octenyl)benzofuran [3.1 g (yield, 97%)] as a colorless oil. 1 H NMR (60 MHz, CDCl3) δ ppm 0.88(t,3H), 1.15-1.54(m,8H), 1.37(s,9H), 1.48(s,9H), 2.31(s,3H), 2.51(m,2H), 6.10(m,1H), 6.27(m,1H), 6.67(s,1H), 7.33(s,1H) Mass 398(M+)

Reference： [1]Current Patent Assignee: Chugai Pharmaceutical (in: Roche); ROCHE HOLDING AG - US5574178, 1996, A

62
ethyl 5-formyl-(R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]-pentanecarboxylate [ No CAS ]
[ 13423-48-8 ]
ethyl (R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]-6Z-tetradecenecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane; water	A.a (K) (K)(a) A solution of 0.51 g of diisopropylamine in 20 ml of THF was treated at 0° C. with 3.13 ml of a 1.6 molar solution of butyl lithium in hexane. The mixture was then cooled to -78° C. and 2.3 g of heptyltriphenylphosphonium bromide were added thereto and the mixture was left at this temperature for 5 minutes. A solution of ethyl 5-formyl-(R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]-pentanecarboxylate in 10 ml of THF was subsequently added dropwise. The mixture was left to stir at room temperature overnight. The reaction mixture was treated with water, extracted with ether, dried and evaporated in vacuo. The residue was chromatographed over silica gel with toluene-ethyl acetate (9:1) and there was obtained 0.5 g of ethyl (R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]-6Z-tetradecenecarboxylate.
	With n-butyllithium; diisopropylamine In tetrahydrofuran; water	1.3 1M. 1M. Preparation of an ester of Formula XIII-A A solution of 0.51 g of diisopropylamine in 20 ml of THF is treated with 3.13 ml of 1.6 molar solution of butyl lithium is hexane at 0° C. The mixture is then cooled to -78° C. and 2.3 g of heptyltriphenyl phosphonium bromide are added thereto and the mixture is left at this temperature for 5 minutes. Subsequently, a solution of ethyl 5-formyl-(R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]pentanecarboxylate in 10 ml of THF is added dropwise thereto. The mixture is left to stir at room temperature overnight. The reaction mixture is treated with water extracted with ether, dried and evaporated in vacuo. The residue is chromatographed over silica gel with toluene-ethyl acetate (9:1) and there is obtained 0.5 g of ethyl (R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]-6Z-tetradecenecarboxylate.

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US4931463, 1990, A
[2]Current Patent Assignee: ROCHE HOLDING AG - US4983746, 1991, A

63
[ 13423-48-8 ]
[ 100-83-4 ]
[ 38697-17-5 ]
3-[(Z)-1-octenyl]phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dimethyl sulfoxide	42 (Z) 3-(1-Octenyl)-phenol EXAMPLE 42 (Z) 3-(1-Octenyl)-phenol Sodium hydride, (3.10 g, 0.077M of a 60% dispersion in oil) was washed by decantation with petroleum ether, bp 60°-80° C. and added to dry, deaerated dimethylsulphoxide, (160 ml), under nitrogen. The mixture was stirred at 75° C. for 0.75 h then cooled to 5° C. A solution of n-heptyltriphenylphosphonium bromide, (34.0 g, 0.077M) in dimethylsulphoxide, (40 ml) was added and the red solution stirred for 15 min. 3-Hydroxybenzaldehyde, sodium salt [9.40 g, 0.077M of 3-hydroxy benzaldehyde in dimethylsulphoxide, (40 ml), treated with one molar equivalent of sodium hydride] was added dropwise at 10° C. and the reaction stirred at 10° C. for 1 h and at room temperature for 3 h. The pale brown mixture was then poured into 10% brine (600 ml), acidified with dilute hydrochloric acid and extracted into hexane, (twice). The combined organic phases were washed with water (twice), brine and then dried, (MgSO4). Evaporation of the solvent and purification by column chromatography using silica gel, eluding with dichloromethane/n-hexane [1:4] yield 7.1 g (45%) of the single Z isomer as a colourless oil. νmax (film) 1490, 1580, 1590, 1610, 3340 cm-1; δ(CDCl3) 0.83 (distorted t, terminal CH3), 1.27 (8H, m, alkylene chain), 2.23 (2H, m, allylic CH2), 5.20 (1H, bs, OH, exchanged with D2 O), 5.60 (1H, d.t, Jd 11 Hz, Jt 7 Hz, =CHCH2), 6.30 (1H, d, J 11 Hz ArCH=), 6.73 (2H, m, aromatics), 7.16 (1H, m, aromatic), 7.56 (1 H, m, aromatic). Found: C, 80.59; H, 9.57; C14 H20 O.0.25H2 O requires: C, 80.53; H, 9.90%.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US4699995, 1987, A

64
[ 629-04-9 ]
[ 22668-36-6 ]
[ 13423-48-8 ]
[ 60669-22-9 ]
[ 2430-94-6 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; triphenylphosphine In hexane	3.1 (1) (1) (Z)-Dodec-5-enoic Acid Heptyltriphenylphosphonium bromide (16.8 g), prepared from 1-bromoheptane and triphenylphosphine analogously to undecyltriphenylphosphonium bromide as described in Example 2(2), is suspended in dry ether (300 ml) and the mixture is treated whilst stirring under nitrogen with 1.7M butyllithium in hexane (36 ml) from a syringe. The resulting bright red solution is cooled to 10° C. and treated dropwise with ethyl 5-oxopentanoate [5.5 g, prepared as described in Example 2 (1B)] in dry ether (37.5 ml). After 10 minutes, the reaction mixture is worked up by the procedure described in Example 2(2) to give ethyl (Z)-dodec-5-enoate as a yellow oil (8.6 g). This oil is treated by the procedure described under Example 2(2) in order to effect hydrolysis and yield (Z)-dodec-5-enoic acid (3.5 g) as an oil (3.5 g).

Reference： [1]Current Patent Assignee: BOSTON SCIENTIFIC CORP - US4803289, 1989, A

65
[1R-[1α,2β(5Z),3β,4α]]-7-[3-Formyl-7-oxabicyclo[2.2.1]hept-2-yl]-5-heptenoic acid, methyl ester [ No CAS ]
[ 13423-48-8 ]
[1R-(1α,2β(5Z),3β(1E),4α)]-7-[3-(1-Octenyl)-7-oxabicyclo[2.2.1]hept-2-yl]-5-heptenoic acid, methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; diisopropylamine; lithium diisopropyl amide In tetrahydrofuran; toluene	2.A A. A. [1R-(1α,2β(5Z),3β(1E),4α)]-7-[3-(1-Octenyl)-7-oxabicyclo[2.2.1]hept-2-yl]-5-heptenoic acid, methyl ester A slurry of triphenylheptylphosphonium bromide (17.64 g, 40 mmoles) in toluene (250 ml) is treated at room temperature with a solution of lithium diisopropylamide (prepared from 1.6 M n-butyl lithium (25 ml, 40 mmoles) and diisopropylamine (6.4 ml, 45 mmoles) in tetrahydrofuran (10 ml). The mixutre is stirred at room temperature for thirty minutes then treated with a solution of [1R-(1α,2β(5Z),3β,4α)]-7-[3-formyl-7-oxabicyclo[2.2.1]hept-2-yl]-5-heptenoic acid, methyl ester (5.32 g, 20 mmoles) in toluene (10 ml). The reaction mixture is stirred at room temperature for one hour then quenched with glacial acetic acid (2.4 g, 40 mmoles). The mixture is poured into brine and extracted with diethylether (3100 ml). The combined ether extracts are washed with water (1100 ml) and brine (1*100 ml), dried over magnesium sulfate and concentrated in vacuo. The residue is triturated with hexane. The precipitated phosphine salts are removed by filtration. The filtrate is concentrated in vacuo. The residue is chromatographed on 10-20μ silica gel (600 ml) eluding with hexane/dichloromethane (1:4) to yield 1.1 g of pure cis product, 530 mg of pure trans product, and 2.4 g of mixed fractions which contained approximately 5% trans product and 95% cis product.

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US4228180, 1980, A

66
[ 64091-14-1 ]
[ 13423-48-8 ]
[ 1150106-67-4 ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: triphenylheptylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 0.75h; Stage #2: (3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-2-oxohexahydro-2H-cyclopenta[b]furan-4-carbaldehyde In tetrahydrofuran for 1.5h;	5.a n-heptylphosphonium bromide (3.185 g, 7.22 mmol) was dried under vacuum for 3 days and was then taken into dry THF (22 mL). Potassium tert-butoxide (7.2 mL, 7.2 mmol, 1 M/THF) was added and the resulting red-orange solution was stirred for 45 min. at room temperature. A solution of (3aR,4R,5R,6aS)-5-(tert-butyldimethylsilyloxy)-2-oxohexahydro-2H-cyclopenta[b]furan-4-carbaldehyde (5-1, 502 mg, 1.78 mmol, Cayman) in 7 mL THF was added by cannula, rinsing with 3 mL THF. After 1.5 h, the reaction was quenched by addition of saturated NH4Cl solution. The resulting mixture was extracted with ethyl acetate (3×) and the combined ethyl acetate solution was dried (Na2SO4), filtered and evaporated. Purification of the residue by flash chromatography on silica gel (Isco Combiflash unit) gave the title compound (595 mg, 91%).

Reference： [1]Current Patent Assignee: ABBVIE INC - US2009/124676, 2009, A1 Location in patent: Page/Page column 6-7

67
[ 13423-48-8 ]
[ 1122-91-4 ]
[ 76287-60-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: triphenylheptylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 0.5h; Stage #2: 4-bromo-benzaldehyde In tetrahydrofuran; hexane at -78 - 20℃;

Reference： [1]Lu, Xuequan; Sun, Chaode; Valentine, William J.; Shuyu; Liu, Jianxiong; Tigyi, Gabor; Bittman, Robert [Journal of Organic Chemistry, 2009, vol. 74, # 8, p. 3192 - 3195]

68
[ 622387-44-4 ]
[ 13423-48-8 ]
4-(4-oct-1-enyl-piperidine-1-sulfonyl)-tetrahydro-pyran-4-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: triphenylheptylphosphonium bromide With lithium hexamethyldisilazane In tetrahydrofuran at 0 - 5℃; for 0.25h; Stage #2: tert-butyl 4-[(4-formylpiperidin-1-yl)sulfonyl]tetrahydro-2H-pyran-4-carboxylate In tetrahydrofuran at 0 - 20℃; for 1.5h;	26.C Part C. Preparation of tert-butyl 4-({4-[1E)-oct-1-enyl]piperdin-1-yl}sulfonyl)tetrahydro-2H-pyran-4-carboxylate An oven-dried, round-bottomed flask fitted with septa and a nitrogen needle was charged with (heptyl)triphenylphosphonium bromide (1.1 g, 2.5 mmol) and tetrahydrofuran (10 mL), resulting in a white slurry. The flask was immersed in an ice bath. Subsequently, a 1 M solution of lithium hexamethyldisilazide in tetrahydrofuran (2.7 mL, 2.7 mmol) was added dropwise, maintaining the reaction temperature at less than 5° C. After complete addition, the mixture was stirred with cooling for 15 min. Then, a solution of the product from Part B (0.75 g, 2.07 mmol) in tetrahydrofuran (2 mL) was added dropwise, again maintaining the reaction temperature at less than 5° C. After complete addition (approximately 15 min), the mixture was stirred with cooling for 15 min. The cooling bath was then removed. The mixture was slowly warmed to room temperature and stirred for 1 hr. Diethyl ether (25 mL) was added to the mixture. This resulted in a tan precipitate, which was removed by vacuum filtration. The filtrate was washed with water (50 mL) and brine (50 mL). The organic layer was dried over magnesium sulfate and concentrated in vacuo. Purification by flash column chromatography (10% ethyl acetate/hexane) yielded 0.66 g of the title compound as a white crystalline solid (72%): 1H NMR (CDCl3) δ; mass spectroscopy (electrospray) m/z=444 (M+H).

Reference： [1]Current Patent Assignee: PFIZER INC - US2005/9838, 2005, A1 Location in patent: Page 149

69
[ 622387-44-4 ]
[ 13423-48-8 ]
[ 622386-96-3 ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: triphenylheptylphosphonium bromide With lithium hexamethyldisilazane In tetrahydrofuran at 0 - 5℃; for 0.25h; Stage #2: tert-butyl 4-[(4-formylpiperidin-1-yl)sulfonyl]tetrahydro-2H-pyran-4-carboxylate In tetrahydrofuran at 5 - 20℃; for 1.25h;	A20.A Part A. Preparation of 4-(4-oct-1-enyl-piperidine-1-sulfonyl)-tetrahydro-pyran-4-carboxylic acid tert-butyl ester An oven-dried, 50 mL glass round-bottom flask was charged with heptyl triphenylphosphonium bromide (1.1 g, 2.5 mmol) and dry tetrahydrofuran (10 mL). The flask was then immersed into an ice bath, and a 1 M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (2.7 mL, 2.7 mmol) was added dropwise while maintaining the temperature at less than 5° C. After complete addition, the reaction mixture was stirred with cooling for 15 min. A solution of the product from Example A4 (0.75 g, 2.1 mmol) in tetrahydrofuran (2 mL) was added dropwise while maintaining the temperature at less than 5° C. After complete addition, the mixture was stirred with cooling for 15 min, and then slowly warmed to room temperature. After stirring for an additional hr, diethyl ether was added to the mixture (25 mL). This resulted in precipitation of a brown solid. The solid was filtered, and the filtrate was washed with water (50 mL) and brine (50 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by flash column chromatography (10% ethyl acetate/hexane) afforded 0.70 g of a colorless crystalline solid product (72% yield). 1H NMR (CDCl3) mixture of isomers in ratio of 7:1, major isomer: δ 0.87 (t, J=6.8 Hz, 3H), 1.22-1.44 (m, 10H), 1.52 (s, 9H), 1.57 (m, 2H), 2.00 (m, 2H), 2.11 (td, J=4.7, 12.6 Hz, 2H), 2.32 (d, J=12.8 Hz, 2H), 2.39 (m, 1H), 2.99 (t,J=12.4 Hz, 2H), 3.30 (t, J=12 Hz, 2H), 3.75 (d, J=12 Hz, 2H), 3.96 (dd, J=4.2, 11.5 Hz, 2H), 5.16 (t, J=9.8 Hz, 1H), 5.33 (td, J=7.6, 10.7 Hz, 1H); Electrospray mass spectrometry showed m/z=444 (M+Na).

Reference： [1]Current Patent Assignee: PFIZER INC - US2005/9838, 2005, A1 Location in patent: Page 292

70
[ 1235555-58-4 ]
[ 13423-48-8 ]
[ 1235555-59-5 ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: triphenylheptylphosphonium bromide With sodium hexamethyldisilazane In tetrahydrofuran at 0 - 20℃; Stage #2: 2-[3,5-di(methoxymethoxy)phenyl]acetaldehyde In tetrahydrofuran at -10 - 20℃;

Reference： [1]Location in patent: experimental part Fiorini, Dennis; Giuli, Sandra; Marcantoni, Enrico; Quassinti, Luana; Bramucci, Massimo; Amantini, Consuelo; Santoni, Giorgio; Buonanno, Federico; Ortenzi, Claudio [Synthesis, 2010, # 9, p. 1550 - 1556]

71
[ 19005-93-7 ]
[ 13423-48-8 ]
[ 58956-36-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: triphenylheptylphosphonium bromide With lithium hexamethyldisilazane In tetrahydrofuran for 0.5h; Stage #2: 1H-indol-2-ylcarboxaldehyde In tetrahydrofuran for 3h;	31.1 To a suspension of heptyl-triphenyl-phosphonium bromide in THF was addedLiHMDS in THF and the mixture was stirred for 30 minutes and then the solution of 1 H- indole-2-carbaldehyde was added to the reaction mixture and stirred for 3 hours. The reaction mixture was treated with saturated ammonium chloride and ethyl acetate. The product was purified by column chromatography.
	Stage #1: triphenylheptylphosphonium bromide With lithium hexamethyldisilazane In tetrahydrofuran at -40℃; Inert atmosphere; Stage #2: 1H-indol-2-ylcarboxaldehyde In tetrahydrofuran at -78 - 25℃; Inert atmosphere;
	Stage #1: 1H-indol-2-ylcarboxaldehyde With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; for 0.5h; Stage #2: triphenylheptylphosphonium bromide In tetrahydrofuran at 20℃; for 3h;

Reference： [1]Current Patent Assignee: MCGILL UNIVERSITY; FLORIDA INSTITUTE OF TECHNOLOGY - WO2010/127452, 2010, A1 Location in patent: Page/Page column 58-59
[2]Gore, Vivek; Patel, Pranav; Chang, Chih-Tsung; Sivendran, Sashikala; Kang, Namin; Ouedraogo, Yannick P.; Gravel, Sylvie; Powell, William S.; Rokach, Joshua [Journal of Medicinal Chemistry, 2013, vol. 56, # 9, p. 3725 - 3732]
[3]Gore, Vivek; Gravel, Sylvie; Cossette, Chantal; Patel, Pranav; Chourey, Shishir; Ye, Qiuji; Rokach, Joshua; Powell, William S. [Journal of Medicinal Chemistry, 2014, vol. 57, # 2, p. 364 - 377]

72
C₇H₈O₅ [ No CAS ]
[ 13423-48-8 ]
(3aR*,4R*,6aS*)-2-hydroxy-4-[(Z)-1-octenyl]perhydrofuro[3,4-b]furan-6-one [ No CAS ]
(3S*,4R*,5R*)-3-hydroxy-4-[(Z)-2-nonenyl]-5-[(Z)-1-octenyl]tetrahydro-2-furanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 36% 2: 16%	Stage #1: triphenylheptylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Inert atmosphere; Stage #2: C₇H₈O₅ In tetrahydrofuran; hexane at -78 - 20℃; for 12h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Hon, Yung-Son; Chen, Hsien-Fan; Kao, Chen-Yi; Luo, Ching-Zong [Tetrahedron, 2010, vol. 66, # 43, p. 8468 - 8475]

73
[ 78999-24-3 ]
[ 13423-48-8 ]
[ 1260379-16-5 ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: triphenylheptylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: 5-benzyloxy-1-pentanal In tetrahydrofuran; hexane; dimethyl sulfoxide at 20℃; for 0.5h; Inert atmosphere;

Reference： [1]Kumaraswamy, Gullapalli; Jayaprakash, Neerasa [Tetrahedron Letters, 2010, vol. 51, # 50, p. 6500 - 6502]

74
[ 32888-40-7 ]
[ 13423-48-8 ]
[ 1262001-36-4 ]

Yield	Reaction Conditions	Operation in experiment
67%	Stage #1: triphenylheptylphosphonium bromide With lithium diisopropyl amide In tetrahydrofuran at -78 - 20℃; for 2.5h; Stage #2: 1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]-2-propanone In tetrahydrofuran at -20℃;

Reference： [1]Location in patent: experimental part Peng, Wei; Ashida, Kazumi; Hirabaru, Toshiaki; Ma, Li-Jian; Inokuchi, Tsutomu [Tetrahedron, 2010, vol. 66, # 51, p. 9714 - 9720]

75
2,3-O-isopropylidene-5-O-trityl-D-ribofuranose [ No CAS ]
[ 13423-48-8 ]
C₃₄H₄₂O₄ [ No CAS ]
[ 1269616-79-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: triphenylheptylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at -10℃; Stage #2: 2,3-O-isopropylidene-5-O-trityl-D-ribofuranose In tetrahydrofuran; hexane at 20℃; optical yield given as %de;	4.2. General procedure for the synthesis of Wittig salts (ylids) and subsequent olefination (b) General procedure: The phosphonium salt was resuspended in THF and cooled to -10 °C. nBuLi (2.5 M solution in hexanes, 2.8 equiv) was added dropwise and the reaction mixture was stirred for 30 min, before a solution of 6 (1 equiv) in dry THF was added. The resulting solution was stirred overnight at room temperature. Upon completion of the reaction, the reaction was quenched with MeOH, followed by 80% MeOH in H2O, and the mixture was extracted with heptane (4 × 20 mL). The combined organic layers were then washed with brine (30 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by purified by flash chromatography using hexanes/EtOAc (10:1) to give the desired products.

Reference： [1]Location in patent: experimental part Veerapen, Natacha; Reddington, Faye; Salio, Mariolina; Cerundolo, Vincenzo; Besra, Gurdyal S. [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 1, p. 221 - 228]

76
[ 13423-48-8 ]
[ 52010-97-6 ]
[ 1338833-96-7 ]
(E)-4-(oct-1-en-1-yl)benzylalcohol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: triphenylheptylphosphonium bromide With lithium hexamethyldisilazane In tetrahydrofuran at 0℃; for 1h; Stage #2: 4-(hydroxylmethyl)benzaldehyde In tetrahydrofuran at -78 - 20℃; for 20h; optical yield given as %de; stereoselective reaction;	2.3. 4-(Oct-1-en-1-yl)benzylalcohol (8) Triphenylheptylphosphonium bromide (4.0588g, 9.1957mmol, 3eq) was suspended in dry THF (9.0 mL) and the mixture was cooled to 0 °C with stirring. LiHMDS (1M in THF, 9.4 mL, 9.4 mmol, 3.1eq) was added dropwise to the mixture and stirred for 1h, followed by cooling to -78 °C. A solution of 4-(methoxymethyl)benzaldhyde3 (6, 0.4133g, 3.036mmol, 1eq) in dry THF (5 mL) was then added dropwise to the phosphoranylide. The solution was allowed to warm to room temperature slowly and stirred for 20h. The mixture was quenched with NH4Cl (20 mL), separated, and the aqueous layer was washed with Et2O (20 mL × 2, 10 mL × 1) and EtOAc (10mL). The organic layers were combined and the solvent removed. Purification was obtained through column chromatography (100 hexanes to 90:10 hexanes:ethyl acetate) to give a faint yellow oil as a mixture of (Z):(E) isomers in a 9:1 ratio (0.5780g, 2.647mmol, 87%). IR (4000-625ν cm-1, NaCl): 3335 (broad OH), 3007, 2955, 2925, 2855, 1457, 1437, 1174, 1014, 722, 695. 1H NMR ((Z)-isomer, 600MHz, CDCl3): δ0.88 (3H, t, J = 7.0Hz), 1.23-1.39 (6H, m), 1.41-1.50 (2H, m), 2.33 (2H, dq, J = 1.8, 7.4Hz), 4.67 (1H, s), 5.68 (1H, dt, J = 7.4, 11.7Hz), 6.40 (1H, d, J = 11.7Hz), 7.25 (2H, d, J = 8.1Hz), 7.33 (2H, d, J = 8.1Hz). 1H NMR ((E)-isomer, 600MHz, CDCl3): δ0.90 (3H, t, J = 6.9Hz), 1.23-1.39 (6H, m), 1.41-1.50 (2H, m), 2.21 (2H, dq, J = 1.3, 7.2Hz), 4.64 (1H, s), 6.23 (1H, dt, J = 6.9, 15.9Hz), 6.37 (1H, d, J = 15.9Hz), 7.26 (2H, d, J = 8.1Hz), 7.32 (2H, d, J = 8.1Hz). 13C NMR ((Z) & (E)-isomers, 150MHz, CDCl3): δ14.2, 14.2, 22.7, 28.8, 29.0, 29.2, 29.5, 30.1, 31.8, 31.9, 33.2, 65.3, 126.2, 127.0, 127.4, 128.4, 129.0, 129.4, 131.5, 133.6, 137.4, 137.6, 139.1, 139.5. MS (ESI+, TOF): Calcd. for C15H22O [M + Ag+] 325.0722; found 325.0720.

Reference： [1]Calzavara, Janice; McNulty, James [Tetrahedron Letters, 2011, vol. 52, # 43, p. 5672 - 5675]

77
[ 13423-48-8 ]
[ 55385-72-3 ]
[ 1353898-79-9 ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: triphenylheptylphosphonium bromide With sodium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; for 0.666667h; Stage #2: (3aS,3bR,7aS,8aR)-2,2,5,5-tetramethyltetrahydro-8aH-[1,3]dioxolo[4′,5′:4,5]furo[3,2-d][1,3]dioxine-8a-carbaldehyde In tetrahydrofuran at -78 - 20℃; for 15h;

Reference： [1]Location in patent: experimental part Brien, Colin O.; Murphy, Paul V. [Journal of Carbohydrate Chemistry, 2011, vol. 30, # 7-9, p. 626 - 640]

78
[ 1577122-24-7 ]
[ 13423-48-8 ]
[ 1577122-28-1 ]

Yield	Reaction Conditions	Operation in experiment
64%	Stage #1: triphenylheptylphosphonium bromide With sodium hexamethyldisilazane In tetrahydrofuran at -5℃; for 0.5h; Inert atmosphere; Stage #2: C₂₇H₅₀O₃Si₂ In tetrahydrofuran at -78℃; for 2.5h; Inert atmosphere;

Reference： [1]Dayaker, Gandrath; Durand, Thierry; Balas, Laurence [Journal of Organic Chemistry, 2014, vol. 79, # 6, p. 2657 - 2665]

79
[ 13423-48-8 ]
[ 137786-97-1 ]
C₂₆H₄₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 20℃;

Reference： [1]Hong, Yeonsun; Sengupta, Sandip; Hur, Wooyoung; Sim, Taebo [Journal of Medicinal Chemistry, 2015, vol. 58, # 9, p. 3739 - 3750]

80
[ 1122011-78-2 ]
[ 13423-48-8 ]
C₂₀H₃₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 20℃;

Reference： [1]Hong, Yeonsun; Sengupta, Sandip; Hur, Wooyoung; Sim, Taebo [Journal of Medicinal Chemistry, 2015, vol. 58, # 9, p. 3739 - 3750]

81
[ 13423-48-8 ]
[ 56495-82-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0 - 20 °C 2: sodium hydride; ethanethiol / N,N-dimethyl-formamide / Reflux 3: oxygen; salcomine / N,N-dimethyl-formamide / 24 h / 20 °C

Reference： [1]Hong, Yeonsun; Sengupta, Sandip; Hur, Wooyoung; Sim, Taebo [Journal of Medicinal Chemistry, 2015, vol. 58, # 9, p. 3739 - 3750]

82
[ 13423-48-8 ]
[ 149806-06-4 ]
2-bromo-5-(oct-1-enyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
11 g	Stage #1: triphenylheptylphosphonium bromide With n-butyllithium In tetrahydrofuran at -40 - 0℃; for 1h; Stage #2: 6-bromonicotinaldehyde In tetrahydrofuran at -15℃; for 3h; Reflux;	Preparation of L1 intermediate 2 [0037] Under anhydrous and anaerobic conditions, in a four-necked rounded-bottom flask, 100 mL dry THF and 33 g(1.2 eq) intermediate 1 are added in sequence, and upon fall of temperature of the reaction system to -40°C, 35 ml nbutyllithium is added dropwise; afterwards, the reaction system is warmed up to 0°C with stirring for 1 hour. Upon fallof temperature of the reaction system to -15°C, 11.6 g (1.2 eq) 2-bromo-5-aldo-pyridine is added dropwise, and thenthe reaction system is warmed up at refluxing with stirring for 3 hours. The reaction liquid is hydrolyzed, extracted withpetroleum ether, and then was subject to column chromatography to give 11 g intermediate 2. [H-NMR (400M, CDCl3)δ (ppm): 8.6 (s, 1H), 7-8 (d, 2H), 6.5 (d, 1H), 6.1 (m, 1H), 1.2-1.4 (m, 8H), 0.95 (m, 3H)].

Reference： [1]Current Patent Assignee: HALATION PHOTONICS CORPORATION - EP2894148, 2015, A1 Location in patent: Paragraph 0037

83
(S)-tert-butyl 4-[(R,E)-1-hydroxy-9-oxonon-2-en-1-yl]-2,2-dimethyloxazolidine-3-carboxylate [ No CAS ]
[ 13423-48-8 ]
(S)-tert-butyl 4-([(R,2E,9Z)]-1-hydroxyhexadeca-2,9-dien-1-yl)-2,2-dimethyloxazolidine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	Stage #1: triphenylheptylphosphonium bromide With sodium hexamethyldisilazane In tetrahydrofuran at 0℃; for 0.5h; Stage #2: (S)-tert-butyl 4-[(R,E)-1-hydroxy-9-oxonon-2-en-1-yl]-2,2-dimethyloxazolidine-3-carboxylate In tetrahydrofuran at -78 - 20℃;	Step 3. ( S )- tert -BUTYL 4-[( R , 2 E , 9 Z ]-1-HYDROXYHEXADECA-2,9-DIEN-1-YL)-2, 2-DIMETHYLOXAZOLIDINE-3-CARBOXYLATE. To a suspensionof heptyltriphenylphosphonium bromide (330 mg,0.75 mmol, 3 eq.) in dry THF (10 ml) at 0°C was added sodiumbis (trimethylsilyl)amide (725 l of 1 M solution in dry THF,2.9 mmol, 2.9 eq.). The solution immediately turned orange andwas stirred at 0°C for 30 min. The resulting solution was cooled to 78°C, and a THF solution (2 ml) of 2 (90 mg, 0.25 mmol, 1 eq.) was added. The reaction was allowed to proceed overnight whereit warmed from 78°C to room temperature (rt) and the colordissipated until white. Saturated aqueous sodium bicarbonatewas added, and the aqueous phase was extracted three times withdiethyl ether (10 ml). The combined organic phases were washedwith brine, dried over anhydrous sodium sulfate, concentrated,and purifi ed by silica gel chromatography (15:85 ethyl acetatehexanes,R f = 0.3) to yield 3 (36 mg, 32% yield) as a colorless oil.1 H-NMR (400 MHz, CDCl 3 ): 0.88 ( t , 3H), 1.25-1.62 ( m , 29H),2.02 ( m , 6H), 3.83 ( m , 1H), 4.02 ( m , 1H), 4.14 ( m , 2H), 5.34 (m, 2H),5.44 ( dd , J = 15.3, 5.2, 1H), 5.73 ( m , 1H). ESI-MS: theoretical m/zfor C 26 H 47 NO 4 Na + (sodium adduct): 460.3397, detected m/z :460.3388, ppm difference: 1.96 ( Fig. 1A , 3 ).

Reference： [1]Zhang, Tejia; Barclay, Lauren; Walensky, Loren D.; Saghatelian, Alan [Journal of Lipid Research, 2015, vol. 56, # 8, p. 1501 - 1510]

84
[ 1196-69-6 ]
[ 13423-48-8 ]
C₁₆H₂₁N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: triphenylheptylphosphonium bromide With lithium hexamethyldisilazane In tetrahydrofuran at -10℃; Stage #2: 1H-indole-5-carboxaldehyde In tetrahydrofuran at -78 - 20℃;	4.7. Synthesis of dyes 4.7.1. 5-Ethyl-1H-indole (5a). General procedure: To a three-necked flask containing a mixture of methyltriphenylphosphonium bromide (2.58 g, 7.23 mmol) and THF was dropwise hexamethyldisilazane lithium salt (7.23 mmol, 1.6 M in THF) at -10 °C. After soluble of methyltriphenylphosphonium bromide, the mixture was dropwise indole-5-carboxyaldehyde (700 mg, 4.83 mmol) in THF (10 mL) at -78 °C over 30 min. The reaction mixture was stirred at -78 °C for additional 1 h, then allowed to stirring at room temperature overnight. The mixture was quenched with satd NH4Cl (aq), then extracted with ethyl acetate. The organic phase was combined and washed with brine, and dried over anhydrous MgSO4. Evaporation of the solvent gave a crude product, which was purified by silica gel chromatograph by EA:hexane (1:5) as eluent. The pale yellow liquid was isolated product of 5-vinyl-1H-indole 4a (459 mg), which was used next reaction without further purification.

Reference： [1]Watanabe, Motonori; Uemura, Naoki; Ida, Shintaro; Hagiwara, Hidehisa; Goto, Kenta; Ishihara, Tatsumi [Tetrahedron, 2016, vol. 72, # 29, p. 4280 - 4287]

85
[ 13423-48-8 ]
[ 206255-41-6 ]
C₂₇H₃₈O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: triphenylheptylphosphonium bromide With potassium hexamethylsilazane In tetrahydrofuran; toluene at -78 - 20℃; for 0.666667h; Inert atmosphere; Stage #2: (3R,4R)-4-Benzyloxy-3-(4-methoxy-benzyloxy)-pentanal In tetrahydrofuran; toluene at -78 - 20℃; for 18h;	Synthesis of 7 To a suspension of heptyltriphenylphosphonium bromide(107.7 mg, 0.244 mmol) in THF (1.5 mL) was added a 0.5 M solutionof KHMDS in toluene (390 lL, 0.195 mmol) at 78 C underan Ar atmosphere. The resulting mixture was stirred at rt for40 min. The reaction mixture was recooled to 78 C, and then asolution of a known aldehyde (6)40 (40.1 mg, 0.122 mmol) in THF(800 lL) was added. After 18 h of stirring at rt, the reaction wasquenched with H2O (1.5 mL), and then was extracted with EtOAc(6 mL 3). The combined organic layers were washed with brine,dried over Na2SO4, filtered, and concentrated in vacuo. The residuewas purified by column chromatography (silica gel, 10-20% EtOAcin hexane) to afford a mixture of an olefin and the by-product(24.0 mg), which was taken to the next step without furtherpurification.

Reference： [1]Ashida, Yoshiki; Yanagita, Ryo C.; Takahashi, Chise; Kawanami, Yasuhiro; Irie, Kazuhiro [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4218 - 4227]

86
[ 13423-48-8 ]
[ 100-52-7 ]
[ 29518-72-7 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: triphenylheptylphosphonium bromide With lithium hexamethyldisilazane In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: benzaldehyde In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Schlenk technique;
	Stage #1: triphenylheptylphosphonium bromide With potassium <i>tert</i>-butylate In diethyl ether for 1h; Reflux; Stage #2: benzaldehyde In diethyl ether for 2h; Reflux;

Reference： [1]Liu, Jianzhong; Wen, Xiaojin; Qin, Chong; Li, Xinyao; Luo, Xiao; Sun, Ao; Zhu, Bencong; Song, Song; Jiao, Ning [Angewandte Chemie - International Edition, 2017, vol. 56, # 39, p. 11940 - 11944][Angew. Chem., 2017, vol. 129, p. 12102 - 12106]
[2]He, Yuli; Liu, Chuang; Yu, Lei; Zhu, Shaolin [Angewandte Chemie - International Edition, 2020, vol. 59, # 48, p. 21530 - 21534][Angew. Chem., 2020, vol. 132, # 48, p. 21714 - 21718,5]

87
C₃₂H₄₀O₂ [ No CAS ]
[ 13423-48-8 ]
C₄₆H₆₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
18.8 g	Stage #1: triphenylheptylphosphonium bromide With potassium <i>tert</i>-butylate In toluene at 5 - 20℃; for 3h; Inert atmosphere; Stage #2: C₃₂H₄₀O₂ In toluene at 20℃; for 6.5h;	10.2 Step 2 After placing heptyltriphenylphosphonium bromide (82.29 g) in a 1 L four-necked flask equipped with a stirrer, the gas in the flask was exchanged with argon. Toluene (520 mL) was placed in the flask and the mixture was cooled to no higher than 5° C. Potassium tert-butoxide (20.92 g) was added and the temperature was raised to room temperature, after which the mixture was stirred at room temperature while thermally insulating for 3 hours. The CM28c (18.0 g) was added to the red slurry produced in the reaction solution, and the mixture was stirred at room temperature while thermally insulating for 6 hours and 30 minutes. Acetic acid (7.2 g) was placed in the reaction solution and stirred therewith for 15 minutes, water and hexane was added and the mixture was stirred at room temperature, after which the aqueous layer was separated off and the organic layer was rinsed with a saturated sodium chloride aqueous solution. Sodium sulfate was added to the obtained organic layer, and after filtering, it was concentrated to obtain a crude product. The crude product was purified with a silica gel column (developing solvent: hexane), active carbon was added to the obtained hexane solution, and the mixture was stirred at 50° C. for 1 hour while thermally insulating. The mixture was then cooled to room temperature and filtered with a filter precoated with Celite, the residue was rinsed several times with hexane, and the filtrates from several rinsings were combined and concentrated to obtain 18.8 g of CM28d as a colorless transparent liquid. LC-MS (APCI, positive): [M+H]+621.

Reference： [1]Current Patent Assignee: Sumitomo Chemical (w/o Dongwoo Fine-Chem); SUMITOMO CHEMICAL COMPANY LIMITED - US9929347, 2018, B2 Location in patent: Page/Page column 218; 220

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	13423-48-8	MDL No. :	MFCD00050249
Formula :	C₂₅H₃₀BrP	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WCZSOHSGMBVYFW-UHFFFAOYSA-M
M.W :	441.38	Pubchem ID :	2724567
Synonyms :

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:

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Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 13423-48-8 ] {[proInfo.proName]}

Quality Control of [ 13423-48-8 ]

Related Doc. of [ 13423-48-8 ]

Product Details of [ 13423-48-8 ]

Safety of [ 13423-48-8 ]

Application In Synthesis of [ 13423-48-8 ]

[ 13423-48-8 ] Synthesis Path-Downstream 1~87

Precautionary Statements-General

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Physical hazards

Health hazards

Environmental hazards

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