Process for the preparation of sphingosine derivatives

Details Process for the preparation of sphingosine derivatives Process for the preparation of sphingosine derivatives

C - Chemistry, Metallurgy

07

H

260/228

C07H 15/10 (2006.01)

Patent

CA 1267891

Abstract The application relates to a new process for the preparation of the sphingosine derivatives described in European Patent Application No. 146,810, of the formula: Image (I) It comprises protecting D-galactose in the 4,6-position and oxidizing it to the corresponding D-threose protected in the 2,4-position, condensing an aliphatic chain (R3) onto the latter by a Wittig reaction, converting the free hydroxyl group into an azido group and splitting off the protective group, protecting the resulting 2-azido-1,3- dihydroxy compound selectively in the 1-position and blocking it in the 3-position, liberating the 1-hydroxy group again, glycosidating the resulting compound or the abovementioned 2-azido-1,3-dihydroxy compound with the 0- trifluoro- or 0-trichloro-acetimidate or the 1-halogen derivative of a 2,3,4,6-0-tetraacyl-D-glucose, splitting off the acyl groups or these and the protective group in the 3-position, converting the azido group into an amino group and.acylating the amino compound with a fatty acid R1-OH. The process gives the compounds of the thera- peutically more active D series in a high yield in rela- tively few stages without resolving diastereomers.

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