Electrochemical generation of glycosyl triflate pools |
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| Authors: | Nokami Toshiki Shibuya Akito Tsuyama Hiroaki Suga Seiji Bowers Albert A Crich David Yoshida Jun-ichi |
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| Affiliation: | Department of Synthetic Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan. |
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| 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. |
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