Selectivity in the SmI2-induced deoxygenation of thiazolylketoses for formyl C-glycoside synthesis and revised structure of C-ribofuranosides

被引：28

作者：

Dondoni, A ^{[1
]}

Formaglio, P ^{[1
]}

Marra, A ^{[1
]}

Massi, A ^{[1
]}

机构：

[1] Univ Ferrara, Dipartmento Chim, Chim Organ Lab, I-44100 Ferrara, Italy

来源：

TETRAHEDRON | 2001年 / 57卷 / 36期

关键词：

deoxygenation; C-glycosides; samarium diiodide; thiazole; Wittig reactions;

D O I：

10.1016/S0040-4020(01)00736-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Deoxygenation of thiazolylketose acetates Using SmI2-(CH2OH)(2) or TMSOTf-Et3SiH affords thiazolyl C-glycosides with opposite alpha/beta ratios. Examination of the thiazolyl alpha- and beta -C-ribofuranoside pair by NOE experiments reveals that the earlier configuration assigned to one of these isomers has to be revised. Having prepared authentic anomeric a- and P-ribofuranose aldehydes from the corresponding thiazolyl C-glycosides by cleavage of the thiazole ring, each aldehyde was transformed into (1 -->6)-C-disaccharides via Wittig olefination with a galactose 6-phosphorane. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：7719 / 7727

页数：9

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