Chemical and Pharmaceutical Bulletin p. 252 - 261 (1993)
Update date:2022-08-03
Topics:
Itaya
Iida
Shimizu
Mizutani
Morisue
Sugimoto
Tachinaka
(R)-[2-Carboxy-2-[(methoxycarbonyl)amino]ethyl]triphenylphosphonium chloride (1) was converted by treatment with anion exchange resin (HCO3-) into the inner salt 13h, which gave a better yield (43%) than 1 in the Wittig reaction with benzaldehyde to afford the [S-(E)]-(2-phenylvinyl)glycine derivative 24. The inner salt 13i bearing an N-benzyioxycarbonyl group was prepared by hydrogenolysis of (R)-[3-benzyloxy-2-[(benzyloxycarbonyl)amino]-3-oxopropyl]triphenylpho sphonium chloride (11e) over palladium on carbon, followed by dehydrochlorination. Hydrogenolysis of 11e over Pearlman's catalyst afforded the unprotected phosphonium chloride 12 (X = Cl). N-tert-Butoxycarbonylation of 12 followed by dehydrochlorination afforded 13j, which was more efficiently prepared through hydrogenolysis of (R)-[3-benzyloxy-2-[(tert-butoxycarbonyl)amino]-3-oxopropyl]triphenylp hosphonium chloride (11f). The usefulness of 13h-j as building blocks for the synthesis of configurationally labile (2-arylvinyl)glycine derivatives was exemplihed by the Wittig reactions with piperonal, which exclusively afforded the (E)-isomers 18h-j with high optical purity in 28-39% yield.
View MoreAnhui Redstar Pharmaceutical Corp., Ltd
Contact:+86-563-5120837
Address:Jingxian Industrial Development Zone, Anhui , China
Contact:+86-371-67759225
Address:No.32, Jinsuo Road, High-tech Zone
NANCHANG QINZHI SCI&TEC.CO.,LTD(expird)
Contact:+86-13687004106
Address:Hero South Road,Hero Zone,Nanchang,Jiangxi,China
Shanghai Send Pharmaceutical Technology Co., Ltd.
website:http://www.shsendpharma.com
Contact:021-58088081, +8613585868794
Address::Room A601, Building 1,NO. 800 Qingdai Road Pudong District Shanghai,China
Shandong Ailitong New Material Co.,Ltd
Contact:+86-536-3226266
Address:zhongjia village, putong town , qingzhou city,Shandong Province,China
Doi:10.1002/ddr.21181
(2014)Doi:10.1016/S0040-4039(98)01897-8
(1998)Doi:10.1021/om400838g
(2013)Doi:10.1246/cl.130463
(2013)Doi:10.1002/jlac.199719970121
(1997)Doi:10.1021/ja409995w
(2013)