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糖基三氟甲磺酸酯库的电化学生成。

Electrochemical generation of glycosyl triflate pools.

作者信息

Nokami Toshiki, Shibuya Akito, Tsuyama Hiroaki, Suga Seiji, Bowers Albert A, Crich David, Yoshida Jun-ichi

机构信息

Department of Synthetic Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan.

出版信息

J Am Chem Soc. 2007 Sep 5;129(35):10922-8. doi: 10.1021/ja072440x. Epub 2007 Aug 14.

DOI:10.1021/ja072440x
PMID:17696345
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4658653/
Abstract

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.

摘要

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。

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