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

✍ Scribed by Zdzislaw M Szulc; Yusuf A Hannun; Alicja Bielawska

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
78 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

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.

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