Silver(I) oxide mediated selective monoprotection of diols in pyranosides

J Org Chem. 2004 Aug 20;69(17):5774-7. doi: 10.1021/jo0497252.

Abstract

The reaction of 4, 6-O-benzylidene-d-pyranosides with a stoichiometric amount of TsCl, AcCl, and BzCl in the presence of silver(I) oxide and a catalytic amount of potassium iodide led to monosubstituted derivatives in high regioselectivity and in good yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Glycosides / analysis
  • Glycosides / chemical synthesis*
  • Glycosides / chemistry*
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Oxides / chemistry*
  • Potassium Iodide / chemistry
  • Pyrans / analysis
  • Pyrans / chemical synthesis*
  • Pyrans / chemistry*
  • Silver Compounds / chemistry*
  • Stereoisomerism

Substances

  • Glycosides
  • Indicators and Reagents
  • Oxides
  • Pyrans
  • Silver Compounds
  • Potassium Iodide
  • disilver oxide