Electrochemical generation of 2,3-oxazolidinone glycosyl triflates as an intermediate for stereoselective glycosylation

Toshiki Nokami, Akito Shibuya, Yoshihiro Saigusa, Shino Manabe, Yukishige Ito, Jun Ichi Yoshida

Research output: Contribution to journalArticlepeer-review

30 Citations (Scopus)

Abstract

Glycosyl triflates with a 2,3-oxazolidinone protecting group were generated from thioglycosides by low-temperature electrochemical oxidation. The glycosyl triflates reacted with alcohols to give the corresponding glycosides β-selectively at low temperatures. However, α-selectivity was observed in the absence of base at elevated reaction temperatures. In situ generated triflic acid promotes the isomerization of β-products to α-products.

Original languageEnglish
Pages (from-to)456-460
Number of pages5
JournalBeilstein Journal of Organic Chemistry
Volume8
DOIs
Publication statusPublished - 2012 Mar 28

Keywords

  • Amino sugar
  • Anomerization
  • Electrochemical oxidation
  • Glycosylation
  • Thioglycoside

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