Synthesis of a versatile building block for the preparation of 6-N-derivatized α-galactosyl ceramides: rapid access to biologically active glycolipids

J Org Chem. 2011 Jan 7;76(1):320-3. doi: 10.1021/jo102064p. Epub 2010 Dec 14.

Abstract

A concise route to the 6-azido-6-deoxy-α-galactosyl-phytosphingosine derivative 9 is reported. Orthogonal protection of the two amino groups allows elaboration of 9 into a range of 6-N-derivatized α-galactosyl ceramides by late-stage introduction of the acyl chain of the ceramide and the 6-N-group in the sugar headgroup. Biologically active glycolipids 6 and 8 have been synthesized to illustrate the applicability of the approach.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrates / chemistry*
  • Galactosylceramides / chemical synthesis*
  • Galactosylceramides / chemistry*
  • Glycolipids / chemistry*
  • Molecular Structure

Substances

  • Carbohydrates
  • Galactosylceramides
  • Glycolipids
  • alpha-galactosylceramide
  • KRN 7000