Total synthesis of alpha-galactosyl ceramide

ORGN 418

Kuanqiang Gao, Department of Chemistry, University of Illinois, 845 W Taylor St, Chicago, IL 60607 and Robert M. Moriarty, Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor, Chicago, IL 60607.
Total synthesis of α-Galactosyl ceramide which posseses very strong anti-hepatitis activity, was achieved starting from L-serine. The stereochemistry of sphingosine derivative was established by addition of 1, 3-dithiane to L-serinal followed by selective reduction of ketone, which was galactosylated to target molecule. This flexible route will provide the access to various glycolipds for SAR studies.