Process for the preparation of sphingosine derivatives

US4937328A · kind A · utility

Assignee

• Solco Basel AG · CH

Inventors

• Richard Schmidt · Konstanz, DE
• Peter Zimmermann · Radolfzell, DE

Key dates

• Filing date: Aug 11, 1986
• Grant date: Jun 26, 1990
• Expiry date: Aug 11, 2006

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y02P20/55
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The invention relates to a new process for the preparation of the sphingosine derivatives described in European Patent Application No. 146,810, of the formula: ##STR1## 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 (R.sup.3) onto the latter by a Wittig reaction, converting the free hydroxyl group into a 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-acetimade or the 1-halogen derivative of a 2,3,4,6-0-tetraacyl-D-glucose, splitting off the acyl groups of 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 R.sup.1 --OH. The process gives the compounds of the therapeutically more active D series in a high yield in relatively few stages without resolving diastereomers.