Triflic acid-mediated synthesis of thioglycosides

Org Biomol Chem. 2019 Sep 28;17(36):8379-8383. doi: 10.1039/c9ob01610d. Epub 2019 Sep 6.

Abstract

An efficient synthesis of thioglycosides from per-acetates in the presence of triflic acid is described. The developed protocol features high reaction rates and product yields. Some reactive sugar series give high efficiency in the presence of sub-stoichiometric trifluoromethanesulfonic acid (TfOH) in contrast to other known protocols that require multiple equivalents of Lewis acids to reach high conversion rates.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Mesylates / chemistry*
  • Thioglycosides / chemical synthesis*
  • Thioglycosides / chemistry

Substances

  • Mesylates
  • Thioglycosides
  • trifluoromethanesulfonic acid