Electrochemical generation of glycosyl triflate pools

Toshiki Nokami; Akito Shibuya; Hiroaki Tsuyama; Seiji Suga; Albert A. Bowers; David Crich; Jun Ichi Yoshida

doi:10.1021/ja072440x

Electrochemical generation of glycosyl triflate pools

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

Research output: Contribution to journal › Article › peer-review

105 Citations (Scopus)

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 (Bu₄-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.

Original language	English
Pages (from-to)	10922-10928
Number of pages	7
Journal	Journal of the American Chemical Society
Volume	129
Issue number	35
DOIs	https://doi.org/10.1021/ja072440x
Publication status	Published - Sept 5 2007
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja072440x

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title = "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 (Bu4-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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T1 - Electrochemical generation of glycosyl triflate pools

AU - Nokami, Toshiki

AU - Shibuya, Akito

AU - Tsuyama, Hiroaki

AU - Suga, Seiji

AU - Bowers, Albert A.

AU - Crich, David

AU - Yoshida, Jun Ichi

PY - 2007/9/5

Y1 - 2007/9/5

N2 - 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 (Bu4-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.

AB - 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 (Bu4-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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Electrochemical generation of glycosyl triflate pools

Abstract

ASJC Scopus subject areas

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