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 l-phosphate dimethyl ester via ba
se-catalyzed N-acylation. (C) 2000 Elsevier Science Ltd. All rights reserve
d.