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Electrochemical generation of glycosyl triflate pools.

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.

SUBMITTER: Nokami T

PROVIDER: S-EPMC4658653 | biostudies-literature | 2007 Sep

REPOSITORIES: biostudies-literature

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Electrochemical generation of glycosyl triflate pools.

Nokami Toshiki T Shibuya Akito A Tsuyama Hiroaki H Suga Seiji S Bowers Albert A AA Crich David D Yoshida Jun-ichi J

Journal of the American Chemical Society 20070814 35

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 trif ...[more]

PMID: 17696345

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