A flexible route towards five-membered ring imino sugars and their novel 2-deoxy-2-fluoro analogues

被引：31

作者：

Ayad, T

Génisson, Y

Broussy, S

Baltas, M

Gorrichon, L

机构：

[1] Univ Toulouse 3, CNRS, LSPCMIB, UMR 5068, F-31062 Toulouse 04, France

[2] CNRS, LCC, F-31077 Toulouse 04, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 2003卷 / 15期

关键词：

sugars; aldehydes; epoxide opening; glycosyltransferase;

D O I：

10.1002/ejoc.200300163

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A flexible route towards five-membered ring imino sugars starting from a chiral alpha,beta-epoxy aldehyde has been developed. The approach relies on the use of the versatile epoxyamine inter-mediate 4, from which regiocontrolled epoxide opening affords diastereoselective access to trisubstituted pyrrolidines. Described here is the nucleophilic attack at C-2 of the pivotal epoxypyrrolidine 10, leading to the biologically relevant imino sugars 1,4-dideoxy-1,4-imino-D-arabinitol (2) and 1,4-dideoxy-1,4-imino-L-galactitol (3) as well as their novel 2-deoxy-2-fluoro analogues, after oxidative manipulation of the vinyl moiety. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).

引用

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页码：2903 / 2910

页数：8

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