Influence of protecting groups on the anomeric equilibrium; case of the 4,6-O-benzylidene acetal in the mannopyranose series

被引：12
|
作者：
Sharma, Indrajeet [1 ]
Bohe, Luis [2 ]
Crich, David [1 ,2 ]
机构：
[1] Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
[2] CNRS, Inst Chim Subst Nat, Ctr Rech Gif, F-91190 Gif Sur Yvette, France
来源：
CARBOHYDRATE RESEARCH | 2012年 / 357卷
关键词：
Mannopyranosides; 4,6-O-Benzylidene acetal; Anomeric equilibrium; Anomeric effect; Conformational analysis; HYDROXYMETHYL GROUP CONFORMATION; POT OLIGOSACCHARIDE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; GLYCOSIDE REACTIVITY; BETA-ARABINOFURANOSIDES; GLYCOSYLATION; DONORS; DERIVATIVES; CHEMISTRY; ACID;
D O I：
10.1016/j.carres.2012.05.025
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：
It is reported that the replacement of the 4- and 6-O-benzyl ethers in 2,3,4,6-tetra-O-benzyl-alpha,beta-mannopyranose by a 4,6-O-benzylidene acetal results in an increased population of the beta-anomer at equilibrium in CDCl3 solution. The phenomenon is considered to arise from the lower steric bulk of the benzylidene acetal that, through diminished buttressing interactions, reduces steric interactions normally present in the b-anomer. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：126 / 131
页数：6
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