Efficient route to orthogonally protected precursors of 2-acylamino-2-deoxy-3-O-substituted-β-D-glucopyranose derivatives and use thereof

被引：13

作者：

Boutet, Julien ^{[1
,2
]}

Kim, Tae Hee ^{[1
]}

Guerreiro, Catherine ^{[1
]}

Mulard, Laurence A. ^{[1
]}

机构：

[1] Inst Pasteur, Unite Chim Biomol, CNRS, URA 2128, F-75015 Paris, France

[2] Univ Paris 05, F-75006 Paris, France

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 36期

关键词：

glucosamine; protecting group; glycosylation; N-trichloroacetyl; Shigella;

D O I：

10.1016/j.tetlet.2008.06.052

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient route to two 3-O-acyl-2-deoxy-4,6-O-isopropylidene-2-trichloroacetamido-D-glucopyranosyl trichloroacetimidate donors is reported. As demonstrated for the 3-O-acetyl derivative, these building blocks are exquisite beta-D-glucosamine donors when reacted either with simple alcohols or with complex oligosaccharides. Besides, their protection pattern is compatible with selective deprotection and subsequent chain elongation at O-3 of the newly incorporated glucosamine residue. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：5339 / 5342

页数：4

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