Chemical modification of some methyl (3,4-di-O-acetyl-2-deoxy-2-hydroxyimino-alpha-D-arabino-hexopyranosid)uronates

被引：1

作者：

Smiatacz, Z

Chrzczanowicz, I

Myszka, H

机构：

[1] Department of Chemistry, University of Gdańsk, 80-952 Gdańsk

来源：

CARBOHYDRATE RESEARCH | 1997年 / 298卷 / 04期

关键词：

O-glycosides; L-serinate glycosides; deoximation; glycuronic acid; azide derivatives; conformation;

D O I：

10.1016/S0008-6215(96)00319-9

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：

Methyl [ethyl 3,4-di-O-acetyl-2-deoxy-2-(Z)-hydroxyimino-alpha-D-arabino-hexopyranosid]uronate (1) and N-tert-butoxycarbonyl-O-[methyl 3,4-di-O-acetyl-2-deoxy-2-(Z)-hydroxyimino-alpha-D-arabino-hexo-pyranosyluronate]-L-serine methyl ester (2) were modified at C-2 and C-3. They have been transformed into the corresponding methyl (2,3,4-tri-O-acetyl-alpha-D-glycopyranosid)uronates by the sequence of reactions 2-C=N-OH --> 2-C=O --> 2-C-OH --> 2-C-OAc. Reaction of 1 and 2 with sodium azide gave the corresponding methyl [ethyl 4-O-acelyl-3-azido-2,3-dideoxy-2-(Z)-hydroxyimino-alpha-D-glycopyranosid]uronates and N-tert-butoxycarbonyl- O-[methyl 4-O-acetyl-3-azido-2,3-dideoxy-2-(Z)-hydroxyimino-alpha-D-glycopyranosyluronate]-L-serine methyl esters. (C) 1997 Elsevier Science Ltd.

引用

页码：341 / 346

页数：6

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