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
收藏
页码：6115 / 6121
页数：7
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