通过相转移催化法合成β-D-甘露吡喃糖叠氮化物的新方法。

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

作者信息

Abronina Polina I, Kachala Vadim V, Kononov Leonid O

机构信息

N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky Prospect, 47, 119991 Moscow, Russian Federation.

出版信息

Carbohydr Res. 2009 Jan 26;344(2):240-4. doi: 10.1016/j.carres.2008.10.027. Epub 2008 Nov 5.

DOI:10.1016/j.carres.2008.10.027

PMID:19013561

Abstract

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.

摘要

开发了一种使用相转移催化从全-O-苯甲酰基-α-D-甘露吡喃糖基溴化物简单立体选择性合成全-O-苯甲酰基-β-D-甘露吡喃糖基叠氮化物的方法。使用二维NOESY核磁共振光谱明确确定了异头O-苯甲酰化的α-和β-D-甘露吡喃糖基叠氮化物C-1处的立体化学。通过在甲醇中用甲醇钠脱苯甲酰基制备了纯的脱保护β-D-甘露吡喃糖基叠氮化物。