1-C-(2′-Oxoalkyl) glycosides as latent α,β-unsaturated conjugates.: Synthesis of aza-C-glycosides by an intramolecular hetero-Michael addition

被引：13

作者：

Yi, T

Wu, AT

Wu, SH

Zou, W

机构：

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

[2] Acad Sinica, Inst Biol Chem, Taipei 115, Taiwan

来源：

TETRAHEDRON | 2005年 / 61卷 / 49期

关键词：

aza-C-glycosides; inhibitors; Michael addition; synthesis;

D O I：

10.1016/j.tet.2005.09.037

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1-C-(2'-Oxoalkyl)-5-azido-5-deoxy-glycofuranosides were used as latent substrates for intramolecular hetero-Michael addition. Reduction of the azido groups by catalytic hydrogenation followed by base treatment produced 2-ester and 2'-ketone aza-C-glycopyranosides. The conjugation addition was stereoselective in favor of aza-C-glycosides with equatorial Substitutions at the pseudo anomeric center. (c) 2005 Elsevier Ltd. All rights reserved.

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收藏

页码：11716 / 11722

页数：7

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