α-Selective ribofuranosylation of alcohols with ribofuranosyl iodides and triphenylphosphine oxide

J Org Chem. 2014 Aug 15;79(16):7656-64. doi: 10.1021/jo500632h. Epub 2014 Jul 24.

Abstract

Ribofuranosylation of a variety of alcohols with ribofuranosyl iodides in the presence of a base and triphenylphosphine oxide afforded the corresponding α-ribofuranosides with diastereoselectivities ≥ 99:1. This reaction can be carried out under mildly basic conditions and is thus compatible with acid-sensitive functional groups.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry*
  • Catalysis
  • Iodides / chemistry*
  • Molecular Structure
  • Organophosphorus Compounds / chemistry*
  • Ribonucleosides / chemistry*

Substances

  • Alcohols
  • Iodides
  • Organophosphorus Compounds
  • Ribonucleosides
  • triphenylphosphine oxide