The use of tri-O-acetyl-D-glucal and -D-galactal in the synthesis of 3-acetamido-2,3-dideoxyhexopyranoses and -hexopyranosides

被引：28

作者：

Liberek, B ^{[1
]}

Dabrowska, A ^{[1
]}

Frankowski, R ^{[1
]}

Matuszewska, M ^{[1
]}

Smiatacz, Z ^{[1
]}

机构：

[1] Univ Gdansk, Fac Chem, PL-80952 Gdansk, Poland

来源：

CARBOHYDRATE RESEARCH | 2002年 / 337卷 / 20期

关键词：

hydrazoic acid; 3-azide-2,3-dideoxy sugar; hydrogenation; 3-amine-2,3-dideoxy saccharide; AZT;

D O I：

10.1016/S0008-6215(02)00288-4

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：

Addition of hydrazoic acid to alpha, beta-unsaturated aldehydes derived from tri-O-acetyl-D-glucal and -D-galactal gave 3-azido-2,3-dideoxyhexopyranoses. These were converted into 1,4,6-tri-O-acetyl-3-azido-2,3-dideoxyhexopyranoses as well as methyl and ethyl glycosides. Hydrogenation of the proamine group in 3-azido-2,3-dideoxy derivatives provided different 3-amino and 3-acetamido sugars. The configuration and conformation of all products were established on the basis of the H-1 and C-13 NMR, IR and polarimetric data. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1803 / 1810

页数：8

共 17 条

[1] SYNTHESIS OF POLYDEOXYDISACCHARIDES AND IODODISACCHARIDES [J].