pH-Dependent Mutarotation of 1-Thioaldoses in Water. Unexpected Behavior of (2S)-D-Aldopyranoses

被引：24

作者：

Caraballo, Remi ^{[1
]}

Deng, Lingquan ^{[1
]}

Amorim, Luis ^{[1
]}

Brinck, Tore ^{[1
]}

Ramstrom, Olof ^{[1
]}

机构：

[1] KTH Royal Inst Technol, Dept Chem, S-10044 Stockholm, Sweden

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 18期

基金：

瑞典研究理事会;

关键词：

SUGARS; THIOOLIGOSACCHARIDES; CONFORMATION; GLYCOSIDES; SOLVATION;

D O I：

10.1021/jo100826e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The pH-dependent mutarotation of 1-thioaldopyranoses in aqueous media has been investigated. Anomerization readily occurred at lower and neutral pH for all aldopyranoses studied, whereas mainly for (2S)-D-aldopyranoses at higher pH. 1-Thio-D-mannopyranose and 1-thio-D-altropyranose showed very strong pH dependence where the anomeric equilibrium ratios changed dramatically from a preference for the beta-anomer at lower pH to the alpha-anomer at higher pH.

引用

页码：6115 / 6121

页数：7

共 57 条

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