From α-1,2-anhydrosugars to C-glycosides:: The influence of Lewis acids and nucleophiles on the stereochemistry

被引：8

作者：

Leeuwenburgh, MA ^{[1
]}

van der Marel, GA ^{[1
]}

Overkleeft, HS ^{[1
]}

van Boom, JH ^{[1
]}

机构：

[1] Leiden Univ, Leiden Inst Chem, NL-2300 RA Leiden, Netherlands

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 2003年 / 22卷 / 7-8期

关键词：

D O I：

10.1081/CAR-120026458

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：

Ring opening of the epoxide function in alpha-1,2-anhydrosugars with alkynyl zinc and titanium compounds proceeds with retention of configuration to afford alpha-C-alkynylglycosides in reasonable to good yields, while the use of the corresponding alkynyltrifluoroborates results in the formation alpha/beta mixtures. Vinyl nucleophiles predominantly afford alpha-products, whereas allyl and allenyl species almost exclusively yield beta-C-glycosides.

引用

页码：549 / 564

页数：16

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