Nokami Toshiki, Shibuya Akito, Tsuyama Hiroaki, Suga Seiji, Bowers Albert A, Crich David, Yoshida Jun-ichi
Department of Synthetic Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan.
J Am Chem Soc. 2007 Sep 5;129(35):10922-8. doi: 10.1021/ja072440x. Epub 2007 Aug 14.
Glycosyl triflates, which serve as important intermediates in glycosylation reactions, were generated and accumulated by the low-temperature electrochemical oxidation of thioglycosides such as thioglucosides, thiogalactosides, and thiomannosides in the presence of tetrabutylammonium triflate (Bu(4)NOTf) as a supporting electrolyte. Thus-obtained solutions of glycosyl triflates (glycosyl triflate pools) were characterized by low-temperature NMR measurements. The thermal stability of glycosyl triflates and their reactions with glycosyl acceptors were also examined.
糖基三氟甲磺酸酯作为糖基化反应中的重要中间体,是通过硫代糖苷(如硫代葡萄糖苷、硫代半乳糖苷和硫代甘露糖苷)在三氟甲磺酸四丁铵(Bu(4)NOTf)作为支持电解质存在下的低温电化学氧化生成并积累的。如此获得的糖基三氟甲磺酸酯溶液(糖基三氟甲磺酸酯库)通过低温核磁共振测量进行表征。还研究了糖基三氟甲磺酸酯的热稳定性及其与糖基受体的反应。