Process for the preparation of sphingosine derivatives

US4952683A · kind A · utility

Assignee

• Solco Basel AG · CH

Inventors

• Roland Tschannen · Basel, CH
• Wolfgang Fraefel · Grolley, CH
• Richard Schmidt · Konstanz, DE
• Rudolf Klager · Pforzheim, DE
• Peter Zimmermann · Radolfzell, DE

Key dates

• Filing date: Dec 24, 1987
• Grant date: Aug 28, 1990
• Expiry date: Dec 24, 2007

Classification

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

Abstract

New compounds of the formula (I)-D and (I)-L as shown in the sheet of formulae are described, for example D- and L-erythro-1-(.beta.-D-glycopyranosyloxy)-3-hydroxy-2-palmitoylamino-4-tran s-octadecene, which exert actions promoting wound healing and cell and tissue regeneration, and can be used therapeutically for the treatment of wounds of any cause. They are prepared in good yield and in a stereochemically homogeneous form from ceramides of the formula (II)-D and/or (II)-L. The process comprises the protection of the 1-hydroxyl group, esterification of the 3-hydroxyl group, elimination of the 1-hydroxyl protective group, reaction with the trifluoroacetimidate or trichloroacetimidate of a 2,3,4,6-tetraacylated D-glucose and elimination of the O-acyl groups. When a D,L-ceramide (II) is used, the esterification of the 3-hydroxyl group is carried out by an optically active acid followed by separation into the diastereomers, or separation into the diastereomers is carried out after the reaction with the D-glucose derivative.