Recent advances in β-l-rhamnosylation

Org Biomol Chem. 2020 May 6;18(17):3216-3228. doi: 10.1039/d0ob00297f.

Abstract

l-Rhamnose forms the key components of important antigenic oligo- and polysaccharides of a variety of pathogens. Obtaining 1,2-cis stereoselectivity in the glycosylation of l-rhamnoside is quite challenging due to the unavailability of neighboring group participation and disfavoring of the anomeric effect and stereoelectronic effect of the substituents on the C-2 axial position. Nevertheless, various methodologies have been developed exploiting diverse pathways for obtaining β-stereoselectivity in the glycosylation of l-rhamnose. This review describes the recent advances in β-l-rhamnosylation and its applications in the total synthesis of β-l-rhamnose-containing biologically important oligosaccharides.

Publication types

  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Borinic Acids / chemistry
  • Catalysis
  • Glycosylation
  • Gold / chemistry
  • Hydrogen Bonding
  • Molecular Structure
  • Oligosaccharides / chemical synthesis*
  • Rhamnose / chemistry*
  • Stereoisomerism

Substances

  • Borinic Acids
  • Oligosaccharides
  • Gold
  • Rhamnose