N-Thiodiglycoloyl derivatives of glucosamine as glycosyl donors

被引：21

作者：

Castro-Palomino, JC ^{[1
]}

Schmidt, RR ^{[1
]}

机构：

[1] Univ Konstanz, Fak Chem, D-78457 Constance, Germany

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 05期

关键词：

D O I：

10.1016/S0040-4039(99)02136-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Thiodiglycoloyl (TDG) protection of O-acetylated glucosamine could be readily carried out with thiodiglycolic anhydride and then treatment with acetic anhydride in pyridine. Ensuing reaction with hydrazinium acetate and then base-catalyzed activation with trichlorocetonitrile afforded N-TDG protected glucosamine donor 3. Glycosylation of accepters 8 and 5 in dichloromethane with TMSOTf as the catalyst gave beta-glycosides 6 and 9 in high yields. For TDG cleavage MeONa/MeOH treatment followed by radical desulfurization with Bu3SnH/AIBN and reacetylation with Ac2O/pyridine was employed, thus giving N-acetyl glucosamine containing compounds 7 and 10 in a convenient, high-yielding procedure. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：629 / 632

页数：4

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