A convenient synthesis of iminosugar-C-glycosides via organometallic addition to N-benzyl-N-glycosylhydroxylamines

被引：46

作者：

Dondoni, A ^{[1
]}

Perrone, D ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 2003年 / 59卷 / 24期

关键词：

nitrones; N-benzyl-N-glycosylhydroxylamines; iminosugars; glycosidase inhibitors; organometallic addition;

D O I：

10.1016/S0040-4020(03)00631-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Benzyl-N-glycosylhydroxylamines were prepared in very good yield via condensation of furanoses and pyranoses with N-benzylhydroxylamine at 110degreesC for 30 min under solvent-free conditions. These anomeric sugar-hydroxylamines exist in equilibrium with the open-chain nitrone form. In fact upon treatment with various organometallic reagents, the corresponding adducts were obtained with good to high diastereoselectivity. These adducts were converted into iminosugar-C-glycosides by reductive dehydroxylation and intramolecular cyclization. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：4261 / 4273

页数：13

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