Epoxidation of C-branched glycals: unexpected stereochemical results and their theoretical rationale

被引：13

作者：

Ernst, C

Piacenza, M

Grimme, S

Klaffke, W

机构：

[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany

[2] Unilever Hlth Inst, Unilever Res & Dev, NL-3130 AT Vlaardingen, Netherlands

来源：

CARBOHYDRATE RESEARCH | 2003年 / 338卷 / 03期

关键词：

C-branched sugars; BP density functional; epoxidation; glycal;

D O I：

10.1016/S0008-6215(02)00406-8

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：

This paper describes the synthesis of C-3 methyl-branched glycosides by epoxidation of partially unblocked L-configured glycals. The stereochemical result depends on the orientation of the allylic hydroxyl group. A theoretical explanation is presented, based on the conformational preferences of the respective glycal half-chair conformations that were estimated by applying the BP density functional and a valence triple-zeta basis set. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：231 / 236

页数：6