Sphingosine-1-phosphate essentially free of L-threo isomer

N,N-dimethylsphingosine-1-phosphate essentially free of L-threo isomer chemically synthesized by a method comprising:

• (A) esterifying the C-3 hydroxyl group of compound 1' to give compound 2' ##STR4## wherein X is a moiety that protects the amino group formed in step (B), (B) selectively deprotecting the C-1 hydroxyl group of said compound 2' to give compound 3' ##STR5## (C) eliminating the protecting moiety X from said compound 3' and then subjecting the product to reductive methylation to give compound 3.sup.a ##STR6## (D) phosphorylating the C-1 hydroxyl group of said compound 3.sup.a followed by hydrolyzing to give compound 3.sup.b ##STR7## (E) deprotecting the C-3 hydroxyl group to give compound 2, which is said N,N-dimethyl-sphingosine-1-phosphate.

N,N,N-trimethylsphingosine-1-phosphate essentially free of L-threo isomer chemically synthesized by a method comprising:

• (A) esterifying the C-3 hydroxyl group of compound 1' to give compound 2' ##STR8## wherein X is a moiety that protects the amino group formed in step (B), (B) selectively deprotecting the C-1 hydroxyl group of said compound 2' to give compound 3' ##STR9## (C) eliminating the protecting moiety X from said compound 3' and then subjecting the product to reductive methylation to give compound 3.sup.a ##STR10## (D) permethylating said compound 3.sup.a followed by treating with a basic anion exchange resin to give compound 3.sup.h ##STR11## (E) phosphorylating the primary hydroxyl group of said compound 3.sup.h followed by hydrolyzing and then deprotecting the C-3 hydroxyl to give compound 3, which is said N,N,N-trimethyl-sphingosine-1-phosphate.

N-acylsphingosine-1-phosphate or N-acetylsphingosine-1-phosphate essentially free of L-threo isomer chemically synthesized by a method comprising:

• (A) esterifying the C-3 hydroxyl group of compound 1' to give compound 2' ##STR12## wherein X is a moiety that protects the amino group formed in step (B), (B) selectively deprotecting the C-1 hydroxyl group of said compound 2' to give compound 3' ##STR13## (C) eliminating the protecting moiety X, then acylating or acetylating the unprotected amino group to give compound 3.sup.i ##STR14## wherein Ac represents acyl or acetyl, (D) phosphorylating the C-1 hydroxyl group of said compound 3.sup.i, followed by hydrolyzing to give compound 3.sup.j ##STR15## (E) deprotecting the C-3 hydroxyl group to give compound 4, which is said N-acylsphingosine-1-phosphate or N-acetylsphingosine-1-phosphate.