An expeditious route to the synthesis of kelampayosides A and B

被引：17

作者：

Duynstee, HI ^{[1
]}

de Koning, MC ^{[1
]}

van der Marel, GA ^{[1
]}

van Boom, JH ^{[1
]}

机构：

[1] Leiden Univ, Leiden Inst Chem, Gorlaeus Labs, NL-2300 RA Leiden, Netherlands

来源：

TETRAHEDRON | 1999年 / 55卷 / 32期

关键词：

carbohydrates; chemoselective glycosidation; apiose; fries-rearrangement;

D O I：

10.1016/S0040-4020(99)00527-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chemoselective NIS/cat. TfOH-mediated glycosylation of ethyl 2,3,4-tri-O-benzoyl-1-thio-beta-D-glucopyranoside (13) with ethyl 2,3-di-O-acetyl-5-O-benzyl-1-thio-alpha/beta-D-erythro-apiofuranoside (4a) gave dimer 14 in an excellent yield. BF . Et2O-catalysed condensation of the alpha-trichloroacetimidate 31, accessible in two steps from 14, with 3,4,5-trimethoxyphenol gave beta-linked derivative 32 followed by deprotection gave Kelampayoside A. Protecting group manipulations of 32 and subsequent caffeoylation of resulting 36 followed by deprotection gave Kelampayoside B. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：9881 / 9898

页数：18

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