Journal of the Chemical Society. Perkin transactions I p. 57 - 60 (1985)
Update date:2022-08-04
Topics:
Diolez, Christian
Sarfati, S. Robert
Szabo, Ladislas
In acidic medium the oxazoline derived from 2-<(3RS)-3-acetoxytetradecanamido>-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose readily eliminates elements of acetic acid: it is transformed into an oxazoline that carries an olefinic substituent having the E configuration; this compound, when treated with an alcohol, yields the corresponding β-D-glucosaminide.No elimination takes place with the analogous 3-hydroxy- or 3-benzyloxy-tetradecanamidoglucosamine derivatives. (3R)-3-benzyloxy-tetradecanoic acid was obtained in 60percent yield upon treatment of methyl (3R)-3-hydroxytetradecanoate in benzene with benzyl bromide, silver oxide, and anhydrous calcium sulphate, followed by saponification.Under similar conditions 3,4,6-tri-O-acetyl-1,2-dideoxy-4',5'-dihydro-2-<(2R)-2-hydroxytridecyl>-α-D-glucopyranoso<2,1-d>oxazole was transformed into the corresponding (2R)-2-benzyloxyoxazoline.
View MoreDongtai Xinyuan Chemical Co., Ltd.
Contact:+86-21-56733000
Address:404F, 99Nong No.117 Zhongtan Rd. Shanghai
Shanghai Longjin Metallic Material Co., Ltd.
website:http://www.shlongjin.cn/
Contact:021-56517503,56502257
Address:No.16, Lane 555, Chengyin Road, Shanghai
Sichuan WeiKeqi Biological Technology Co., Ltd.
website:https://www.weikeqi-biotech.com/en
Contact:86-028-81700200
Address:sichuan Chengdu Qingjiang Zhonglu 63号
Beijing Apis Biotechnology Co., Ltd.
Contact:86-010-67856775-8551
Address:NO.4PUHUANGYU ROAD,FENTAI DISTRICT, BEIJING, CHINA
Contact:+86-27-85733560
Address:NO.308,QINGNIAN RD.,WUHAN,CHINA
Doi:10.1021/jm00145a006
(1985)Doi:10.1021/ja00301a017
(1985)Doi:10.1016/S0040-4039(98)02502-7
(1999)Doi:10.1021/jo00215a037
(1985)Doi:10.1111/cbdd.13576
(2019)Doi:10.1021/jm00147a014
(1985)
