Method of preparing sphingosine derivatives

Details Method of preparing sphingosine derivatives Method of preparing sphingosine derivatives

C - Chemistry, Metallurgy

07

C

260/606, 260/604

C07C 209/54 (2006.01) C07C 215/24 (2006.01) C07C 263/06 (2006.01) C07C 271/16 (2006.01) C07D 263/06 (2006.01)

Patent

CA 1340549

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.

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