Efficient synthesis of alpha-C-galactosyl ceramide immunostimulants: use of ethylene-promoted olefin cross-metathesis

Org Lett. 2004 Oct 28;6(22):4077-80. doi: 10.1021/ol0482137.

Abstract

[reaction: see text] Olefin cross-metathesis has been used to prepare alpha-C-galactosylceramide derivatives. The metathesis process merged vinyl and propenyl glycosides with vinyl derivatives of phytosphingosine. The use of ethylene enhanced the yield of the methathesis step.

Publication types

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

MeSH terms

  • Adjuvants, Immunologic / chemical synthesis*
  • Adjuvants, Immunologic / pharmacology
  • Alkenes / chemistry*
  • Ethylenes / chemistry*
  • Galactosylceramides / chemical synthesis*
  • Galactosylceramides / pharmacology
  • Glycosides / chemistry
  • Molecular Structure
  • Sphingosine / analogs & derivatives
  • Vinyl Compounds / chemistry

Substances

  • Adjuvants, Immunologic
  • Alkenes
  • Ethylenes
  • Galactosylceramides
  • Glycosides
  • Vinyl Compounds
  • ethylene
  • Sphingosine