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

Z. M. Szulc; Y. A. Hannun; A. Bielawska

doi:10.1016/S0040-4039(00)01361-7

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

Z. M. Szulc
, Y. A. Hannun
, A. Bielawska

Cancer Center

Medical University of South Carolina

Research output: Contribution to journal › Article › peer-review

28 Scopus citations

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 1-phosphate dimethyl ester via base-catalyzed N-acylation. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	7821-7824
Number of pages	4
Journal	Tetrahedron Letters
Volume	41
Issue number	41
DOIs	https://doi.org/10.1016/S0040-4039(00)01361-7
State	Published - Oct 7 2000

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title = "A facile regioselective synthesis of sphingosine 1-phosphate and ceramide 1-phosphate",

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 1-phosphate dimethyl ester via base-catalyzed N-acylation. (C) 2000 Elsevier Science Ltd.",

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T1 - A facile regioselective synthesis of sphingosine 1-phosphate and ceramide 1-phosphate

AU - Szulc, Z. M.

AU - Hannun, Y. A.

AU - Bielawska, A.

PY - 2000/10/7

Y1 - 2000/10/7

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/0034619128

U2 - 10.1016/S0040-4039(00)01361-7

DO - 10.1016/S0040-4039(00)01361-7

M3 - Article

AN - SCOPUS:0034619128

SN - 0040-4039

VL - 41

SP - 7821

EP - 7824

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 41

ER -

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

Abstract

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