Method of preparing sphingosine derivatives

Abstract From the Canadian patent

A method of preparing a substituted derivative of sphingosine comprising the steps of reducing serine methyl ester by a hydride reagent to form an aldehyde or aldehyde derivative, adding acetylide anions to the aldehyde to form an erythro-isomer of propargyl alcohol and inverting the propargyl alcohol by S N2 inversion to form a threo-isomer. Either isomer can then be de-protected to form an alkyne with a 2-amino-propane 1,3 diol head group; this alkyne can be reduced to form sphingosine or a sphingosine derivative which can be functionalized at the 4 and 5 positions to form a substituted derivative of sphingosine.