A stereoselective ring-closing glycosylation via nonglycosylating pathway

J Org Chem. 2014 Jun 20;79(12):5834-41. doi: 10.1021/jo5006763. Epub 2014 Jun 6.

Abstract

Two glycosyl partners were first coupled with as ester linkage, which upon reductive acetylation produced an α-acetoxy ether group. The subsequent activation with TfOH triggered the ring-closing process and provided the corresponding glycosidic bond in high β-selectivity without relying on neighboring group participation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylation
  • Cyclization
  • Glycosides / chemistry*
  • Glycosylation*
  • Molecular Structure
  • Stereoisomerism*

Substances

  • Glycosides