Synthesis of Glycosphingolipids and Psychosines

Abstract

As components of biological membranes, glycolipids are of great importance. By reversing the usual order of steps in the synthesis, the yields obtained by a known method have been dramatically improved: the azidosphingosine and not the ceramide is glycosylated first by means of the trichloroacetimidate method. O-Glucopsychosine (1, NH2 instead of NHCOC15H31) can thereby be facilely acylated to give the glucocerebroside 1.