KTH-Royal Institute of Technology, Department of Chemistry, Teknikringen 30, S-10044 Stockholm, Sweden.
J Org Chem. 2010 Sep 17;75(18):6115-21. doi: 10.1021/jo100826e.
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 β-anomer at lower pH to the α-anomer at higher pH.
本文研究了 1-硫代醛糖在水介质中的 pH 依赖性变旋。所有研究的醛糖在较低和中性 pH 下很容易发生端基异构化，而在较高 pH 下主要是（2S）-D-醛糖。1-硫代-D-甘露吡喃糖和 1-硫代-D-阿洛吡喃糖表现出很强的 pH 依赖性，其中端基异构体平衡比从较低 pH 下β-端基异构体的优势显著变化到较高 pH 下的α-端基异构体。
