Highly efficient and mild method for regioselective de-O-benzylation of saccharides by Co2(CO)8-Et3SiH-CO reagent system

Org Lett. 2010 Feb 5;12(3):536-9. doi: 10.1021/ol902717y.

Abstract

A highly efficient and mild method for the de-O-benzylation of protected saccharides was developed by transforming terminal benzyl ethers into silyl ethers using Co(2)(CO)(8)-Et(3)SiH under 1 atm of CO. The method was successfully used for the de-O-benzylation of perbenzylated monosaccharides with various anomeric protecting groups, as well as natural disaccharides and trisaccharides such as sucrose, raffinose, and melezitose in good yields (>80%).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzene Derivatives / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Molecular Structure
  • Trisaccharides / chemical synthesis*
  • Trisaccharides / chemistry

Substances

  • Benzene Derivatives
  • Trisaccharides