EFFICIENT AND STEREOSELECTIVE 1,2-CIS-GLYCOSIDE FORMATION OF 5-THIOALDOPYRANOSES - GLYCOSYLATION WITH PERACETYLATED 5-THIO-D-ARABINOPYRANOSYL AND 5-THIO-L-FUCOPYRANOSYL-TRICHLOROACETIMIDATES

被引：33

作者：

HASHIMOTO, H

IZUMI, M

机构：

[1] Department of Life Science, Faculty of Bioscience and Biotechnology, Tokyo Institute of Technology, Midori-ku, Yokohama, 227, Nagatsuta

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 31期

关键词：

D O I：

10.1016/S0040-4039(00)74054-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Trichloroacetimidate method was proved to be effective for 5-thio-D-arabinopyranosylation and 5-thio-L-fucopyranosylation of N-acetyl-D-glucosaminides and D-galactosides. In these 5-thioglycosylation the neighboring group participation of 2-0-acetyl function was not decisive of anomeric stereoselectivity to give 1,2-cis pseudodisaccharides predominantly. Allyl 2-O-(5-thio-alpha-L-fucopyranosyl)-beta-D-galactopyranoside showed potent inhibitory activity toward alpha-L-fucosidase (Ki = 30muM).

引用

页码：4949 / 4952

页数：4

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