Useful Syntheses of erythro- and threo-N-Oleoyl-D-sphingosines (Ceramides) and Galactosylceramides (Cerebrosides) from L-Serine

Article abstract of DOI:10.1021/jo00335a015

The 4-(carbomethoxy)-2-phenyl-Δ²-oxazoline formed from L-serine provides the basis for a useful synthesis of ceramides and cerebrosides.The natural erythro configuration and its threo epimer are formed in equal amounts but are readily separated chromatographically, so that both epimers are available for experiments in which the properties of erythro and threo configurations are to be compared.The method produces the final cerebroside product on a scale of 100 mg or more.The optical purity of the product was shown to be close to 100percent.In addition to the threo epimer, other analogues of the natural cerebrosides with different chain le ngths and stereochemistries should be readily available by using the route developed.Such molecules are of interest to us for (13)C NMR and related studies of membrane organization.