A concise synthesis of 4-nitrophenyl 2-azido-2-deoxy- and 2-acetamido-2-deoxy-D-mannopyranosides

被引：13
|
作者：
Popelová, A [1 ]
Kefurt, K [1 ]
Hlaváckova, M [1 ]
Moravcová, J [1 ]
机构：
[1] Inst Chem Technol, Dept Chem Nat Cpds, CR-16628 Prague, Czech Republic
来源：
CARBOHYDRATE RESEARCH | 2005年 / 340卷 / 01期
关键词：
2-azido-2-deoxymannoside; 2-acetamido-2-deoxymannopyranoside; 4-nitrophenyl glycoside; migration of acetyl group;
D O I：
10.1016/j.carres.2004.11.002
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：
4-Nitrophenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha- and beta1-D-mannopyranosides were prepared from methyl 4,6-O-benzylidene-alpha-D-glucopyranoside and 1,3,4,6-tetra-O-acetyl-alpha-D-glucopyranose, respectively. Chemoselective reduction of both azides with hydrogen sulfide readily afforded 4-nitrophenyl 2-acetamido-4,6-di-O-acetyl-2-deoxy-alpha-D- and -beta-D-mannopyranosides in higher yields than reduction with triphenylphosphine or a polymer-supported triarylphosphine. Subsequent de-O-acetylation yielded 4-nitrophenyl 2-acetamido-2-deoxy-alpha-D-mannopyranoside and 4-nitrophenyl 2-acetamido-2-deoxy-beta-D-mannopyranoside in 20 % and 44 % overall yields, respectively. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：161 / 166
页数：6
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