Stereoselective synthesis of [13C]methyl 2-[15N]amino-2-deoxy-β-D-glucopyranoside derivatives

被引：23

作者：

Boulineau, FP ^{[1
]}

Wei, A ^{[1
]}

机构：

[1] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA

来源：

CARBOHYDRATE RESEARCH | 2001年 / 334卷 / 04期

关键词：

stereoselectivity; C-13-labeling; N-15-labeling; heteronuclear coupling constants;

D O I：

10.1016/S0008-6215(01)00203-8

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：

Efficient syntheses of three [C-13]methyl 2-[N-15]amino-2-deoxy-beta -D-glucopyranoside derivatives are described. Amination of the D-glucal with (saltmen)Mn(N-15) proceeded with 11:1 stereoselectivity favoring the gluco configuration subsequent methylation of the [N-15]lactol using [C-13]iodomethane and silver(I) oxide afforded the doubly labeled beta glucoside in high yield. This compound served as the common precursor for three [C-13]methyl 2-[N-15]aminoglucosides: (2-[N-15]trifluoroacetyl-), (2-[N-15]acetyl-), and (2-[N-15]azido-). Selected heteronuclear coupling constants are reported. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：271 / 279

页数：9

共 16 条

[1] Metal catalyzed diazo transfer for the synthesis of azides from amines [J].