A novel synthesis of β-D-mannopyranosyl azide by phase transfer catalysis

被引：6

作者：

Abronina, Polina I. ^{[1
]}

Kachala, Vadim V. ^{[1
]}

Kononov, Leonid O. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia

来源：

CARBOHYDRATE RESEARCH | 2009年 / 344卷 / 02期

基金：

俄罗斯基础研究基金会;

关键词：

Glycosyl azides; 1,2-cis-Mannopyranosyl azide; Phase transfer catalysis; Stereoselectivity; NMR spectroscopy; 1,2-CIS O-GLYCOSYLATION; X-RAY STRUCTURE; CARBOHYDRATE-CHEMISTRY; STAUDINGER LIGATION; CYCLOADDITION; TRIAZOLES; UTILITY; SUGARS;

D O I：

10.1016/j.carres.2008.10.027

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A simple stereoselective synthesis of per-O-benzoyl-beta-D-mannopyranosyl azide from per-O-benzoyl-alpha-D-mannopyranosyl bromide using phase transfer catalysis was developed. The stereochemistry at C-1 of the anomeric O-benzoylated alpha- and beta-D-mannopyranosyl azides was unambiguously established using 2D NOESY NMR spectroscopy. Pure deprotected beta-D-mannopyranosyl azide was prepared by debenzoylation with sodium methoxide in methanol. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：240 / 244

页数：5

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