A facile regioselective synthesis of sphingosine 1-phosphate and ceramide 1-phosphate

Article abstract of DOI:10.1016/S0040-4039(00)01361-7

A novel regioselective synthesis of D-erythro-sphingosine 1-phosphate and D-erythro-ceramide 1-phosphate is described. The synthesis is based upon (1) in situ oxidative phosphorylation of the primary hydroxyl group in N-Boc-D-erythro-sphingosine utilizing trimethyl phosphite and carbon tetrabromide in pyridine, (2) chemoselective deprotection of the 1-O-phosphate and/or 2-amino groups with trimethylsilyl bromide or chloride, and (3) introduction of the fatty acid moiety into sphingosine 1-phosphate dimethyl ester via base-catalyzed N-acylation. (C) 2000 Elsevier Science Ltd.