Electrochemical generation of glycosyl triflate pools

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

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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 (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 languageEnglish
Pages (from-to)10922-10928
Number of pages7
JournalJournal of the American Chemical Society
Volume129
Issue number35
DOIs
Publication statusPublished - Sep 5 2007
Externally publishedYes

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ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Nokami, T., Shibuya, A., Tsuyama, H., Suga, S., Bowers, A. A., Crich, D., & Yoshida, J. I. (2007). Electrochemical generation of glycosyl triflate pools. Journal of the American Chemical Society, 129(35), 10922-10928. https://doi.org/10.1021/ja072440x