Journal of Organic Chemistry p. 4018 - 4023 (1982)
Update date:2022-08-04
Topics: Mycolic acids (E)and (Z)-threo-2-Docosyl-3-hydroxytetracont-21-enoate
Huang, Harry C.
Rehmann, Jill K.
Gray, Gary R.
The ethyl esters of (E)- and (Z)-2-docosyl-3-hydroxytetracont-21-enoate (4a and 4b, respectively) have been prepared by a route involving alkylation of the dianion of ethyl 2-docosyl-3-oxobutyrate (2) with either (E)-1-iodo-17-hexatriacontene (14c) or (Z)-1-iodo-17-hexatriacontene (13c) and subsequent borohydride reduction of the intermediate β-keto esters (3a and 3b, respectively).Resolution of the 3:2 mixture of erythro and threo diastereomers of 4a and 4b was accomplished by high-performance liquid chromatography, employing phenacyl ester derivatives.The 1H NMR spectra of phenacyl (E)-threo-2-docosyl-3-hydroxytetracont-21-enoate (6a) and phenacyl (Z)-threo-2-docosyl-3-hydroxytetracont-21-enoate (6b) were identical with the spectra previously reported for the phenacyl esters of the naturally occurring monoalkene mycolic acids from Mycobacterium smegmatis (see ref 10).An examination of the phenacyl ester of the epoxide derivative of the naturally occurring mycolic acid by 1H NMR spectroscopy established that it was a 93:7 mixture of the Z and E isomers, respectively, of phenacyl threo-2-docosyl-3-hydroxytetracont-21-enoate.
View MoreShanghai Rainbow Chemistry Co., Ltd.
Contact:+86-21-64968086-5815/5812
Address:3rd floor, Building 7, 251 Faladi Road, Zhangjiang Hi-Tech Park, Pudong District, Shanghai, P.R. China
Xi'an Kaixiang Photoelectric Technology Co., Ltd
website:http://www.kxmaterials.com/
Contact:86-29-15991651477
Address:Building 6, Biopharmaceutical Industry R&D Cluster Base, No. 16, Caotang 4th Road, Caotang Science and Technology Industrial Base, High-tech Zone, Xi'an City, Shaanxi Province, China
JiangXi Hong Run Chemical Co., Ltd
Contact:+86-0791-88521351
Address:XingHuo industrial zone in YongXiu county
Shanghai Potomer International Trade CO., LTD
Contact:+86-21-61397128
Address:Room 304,No.505 ,Caoyang Road.Shanghai,China
Hebei DaPeng Pharm & Chem Co., Ltd.
Contact:86-317-7298678,0576-88861898 88861908
Address:West Songmen Village, East Songmen Town, Wuqiao, Cangzhou, Hebei ,China
Doi:10.1039/P19930000653
(1993)Doi:10.1021/ol0624676
(2006)Doi:10.1039/c4sc03358b
(2015)Doi:10.1021/jo00197a019
(1984)Doi:10.1021/ja00220a021
(1988)Doi:10.1016/j.tet.2006.09.099
(2006)