Hydrolysis of α- and β-glycosides.: New experimental data and modeling of reaction pathways

被引：29

作者：

Deslongchamps, P ^{[1
]}

Li, SG ^{[1
]}

Dory, YL ^{[1
]}

机构：

[1] Univ Sherbrooke, Inst Pharmacol, Dept Chim, Sherbrooke, PQ J1H 5N4, Canada

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 04期

关键词：

D O I：

10.1021/ol036220+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cyclization of oxocarbenium ion conformers 6alpha and 6beta (from 11E and 11Z) gave only the beta-glycoside 1beta, and the addition of methanol to the oxocarbenium ion 3 yielded mainly the alpha-glycoside 1alpha with both experiments being carried out under kinetically controlled conditions. RHF/6.31G* calculations reproduce well these experimental results and show that the endocyclic and the exocyclic C-O bond cleavage processes can compete in the hydrolysis of 1beta, whereas 1alpha gets hydrolyzed by exocyclic C-O bond cleavage only.

引用

页码：505 / 508

页数：4

共 31 条

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