The first synthesis of a thioglycoside analogue of the immunostimulant KRN7000

Org Lett. 2008 Oct 16;10(20):4641-4. doi: 10.1021/ol8019555. Epub 2008 Sep 23.

Abstract

The first total synthesis of a thioglycoside analogue of KRN7000, a potential immunostimulant, is described. Two key intermediates are alpha-galactosyl thiol 4 and phytosphingosine derivative 5, which were both prepared from D-galactose.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adjuvants, Immunologic / chemical synthesis*
  • Adjuvants, Immunologic / chemistry
  • Galactose / chemistry
  • Galactosylceramides / chemical synthesis*
  • Galactosylceramides / chemistry
  • Molecular Structure
  • Sulfhydryl Compounds / chemistry
  • Thioglycosides / chemistry*

Substances

  • Adjuvants, Immunologic
  • Galactosylceramides
  • Sulfhydryl Compounds
  • Thioglycosides
  • KRN 7000
  • Galactose