The application of the intermediate 2-methyl-glyco-[2,1-d]-2-oxazolines for glycoside synthesis

被引：4

作者：

Pertel, SS ^{[1
]}

Chirva, VY ^{[1
]}

Kadun, AL ^{[1
]}

Kakayan, ES ^{[1
]}

机构：

[1] Natl Taurida Univ, Dept Organ Chem, UA-95007 Simferopol, Crimea, Ukraine

来源：

CARBOHYDRATE RESEARCH | 2000年 / 329卷 / 04期

关键词：

glycosyl halides; halide-ion catalysis; 1,2-trans-glycosides of 2-acylamino-2-deoxysugars; glyco-[2,1-d]-2-oxazolines; 1,2-trans-glycosaminides anomerisation;

D O I：

10.1016/S0008-6215(00)00237-8

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：

The synthesis of 2-acylamino-2-deoxysugars 1,2-trans-glycosides is described via the oxazolinium salt generated from an O,N-acetylated 1,2cis-glycosyl halide of 2-amino-2-deoxysugar under the conditions of halide-anion catalysis. This salt was then interacted with alcohol to form the corresponding 1,2-trans-glycoside. A method for removing the generated hydrogen chloride is described. The conditions of this synthesis allow glycosides with acid-labile functional groups to be obtained. Suppression of the anomerisation of 1,2-trans-glycosides was achieved by the introduction of N,N'-dicyclohexyl urea into the reaction medium. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：895 / 899

页数：5