Regio- and stereo-selective synthesis of aryl 2-deoxy-C-glycopyranosides by palladium-catalyzed Heck coupling reactions of glycals and aryl iodides

Org Biomol Chem. 2009 Sep 21;7(18):3855-61. doi: 10.1039/b909248j. Epub 2009 Jul 20.

Abstract

The Heck coupling of aryl iodides with pyranoid glycals using a catalytic amount of Pd(OAc)(2) to form pyranoid aryl C-glycosides has been achieved. The reaction takes place smoothly in the presence of Ag(2)CO(3) and Cu(OAc)(2) (or DMSO) in acetonitrile. This arylation process, which occurs in a highly regio- and stereo-selective manner, provides a simple, mild, and efficient approach to the synthesis of aryl 2-deoxy-C-glycopyranosides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Ethers / chemistry*
  • Glycosides / chemical synthesis*
  • Glycosides / chemistry*
  • Glycosylation
  • Halogens / chemistry
  • Iodine / chemistry*
  • Palladium / chemistry*
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Ethers
  • Glycosides
  • Halogens
  • Palladium
  • Iodine