Efficient synthesis of alpha-galactosyl ceramide analogues using glycosyl iodide donors

Org Lett. 2005 May 12;7(10):2063-5. doi: 10.1021/ol050659f.

Abstract

The combination of reactive galactosyl iodide donors with electron-rich acceptor lipids provides highly stereoselective and efficient routes to alpha GalCer analogues. Using per-O-silylated donors, key intermediates can be obtained in a three-step, one-pot sequence providing useful constructs for analogue development.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Galactosylceramides / chemical synthesis*
  • Galactosylceramides / chemistry
  • Glycosides / chemistry*
  • Iodides / chemistry*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Galactosylceramides
  • Glycosides
  • Iodides