Synthesis of thio-C-glycosides from 2′-carbonylalkyl C-glycosides by a tandem β-elimination and intramolecular hetero-Michael addition

被引：13

作者：

Zou, W

Lacroix, E

Wang, ZR

Wu, SH

机构：

[1] Natl Res Council Canada, Inst Biol Sci, Ottawa, ON K1A 0R6, Canada

[2] Acad Sinica, Inst Biol Chem, Taipei, Taiwan

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 24期

关键词：

synthesis; thio-glycoside; C-glycoside; beta-elimination; cycloaddition;

D O I：

10.1016/S0040-4039(03)01039-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2'-Carbonyl 5-S-acetyl-C-glycofuranosides and 2'-carbonyl 4-S-acetyl-C-glycopyranosides were converted in good yields to respective 5-thio-C-glycopyranosides and 4-thio-C-glycofuranosides under base treatment. The transformation was resulted from beta-elimination on 2'-carbonyl C-glycoside to form alpha,beta-conjugated aldehyde (or ketone) and following intramolecular hetero-Michael addition by the thiol group. Crown Copyright (C) 2003 Published by Elsevier Science Ltd. All rights reserved.

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收藏

页码：4431 / 4433

页数：3

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