A convenient synthesis of alkyl D-glycofuranosiduronic acids and alkyl D-glycofuranosides from unprotected carbohydrates

被引：68

作者：

Ferrières, V ^{[1
]}

Bertho, JN ^{[1
]}

Plusquellec, D ^{[1
]}

机构：

[1] Ecole Natl Super Chim Rennes, CNRS, Lab Chimie Organ & Subst Nat, F-35700 Rennes, France

来源：

CARBOHYDRATE RESEARCH | 1998年 / 311卷 / 1-2期

关键词：

glycosylation; unprotected carbohydrates; alkyl D-glycofuranosiduronic acids; alkyl D-glycofuranosides;

D O I：

10.1016/S0008-6215(98)00197-9

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：

O-Glycosylation of a variety of long chain alcohols with totally unprotected uronic acids (D-glucuronic and D-galacturonic acids) and neutral carbohydrates (D-glucose, D-galactose, D-mannose and D-glucofuranurono-6,3-lactone), performed in heterogeneous media and promoted by Lewis acids (ferric chloride or boron trifluoride diethyl etherate), afforded alkyl D-glycofuranosiduronic acids and alkyl D-glycofuranosides, respectively, in high yields. Both chemoselectivity and anomeric stereoselectivity were enhanced by complexing agents, i.e. calcium or barium chloride. (C) 1998 Elsevier Science Ltd. All rights reserved

引用

页码：25 / 35

页数：11

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