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

Citation
Zm. Szulc et al., A facile regioselective synthesis of sphingosine 1-phosphate and ceramide 1-phosphate, TETRAHEDR L, 41(41), 2000, pp. 7821-7824
Citations number
43
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
41
Year of publication
2000
Pages
7821 - 7824
Database
ISI
SICI code
0040-4039(20001007)41:41<7821:AFRSOS>2.0.ZU;2-8
Abstract
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.