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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]

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