On the stereochemistry of aryl C-glycosides: Unusual behavior of bis-TBDPS protected aryl C-olivosides

被引：108

作者：

Hosoya, T ^{[1
]}

Ohashi, Y ^{[1
]}

Matsumoto, T ^{[1
]}

Suzuki, K ^{[1
]}

机构：

[1] KEIO UNIV,DEPT CHEM,KOHOKU KU,YOKOHAMA,KANAGAWA 223,JAPAN

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 05期

关键词：

D O I：

10.1016/0040-4039(95)02227-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A D-olivosyl donor in which the C(3) and C(4) hydroxyls are both protected by an extremely bulky group, t-BuPh(2)Si, undergoes aryl C-glycosidation in an alpha-selective manner, and the product configuration remains unchanged under various Lewis acid conditions. The features are rationalized by the ring flipping of the pyranoside ring (C-1(4)) in the glycosyl donor and the C-glycoside product, due to the severe repulsion of the siloxy groups.

引用

页码：663 / 666

页数：4