Process for the preparation of sphingosin derivatives

Abstract

Abstract Examples of the compounds are D- and L-erythro-1-( beta -D- glucopyranosyloxy)-3-hydroxy-2-palmitoylamino-4-trans-octadecene, and the compounds promote wound healing and have a cell- and tissue-regenerating action and can be used for the treatment of wounds of any origin. They are prepared from ceramides of the formula (II)-D and/or (II)-L in good yield and in stereochemically pure form. The process comprises protecting the 1-hydroxyl group, esterifying the 3-hydroxyl group, eliminating the 1-hydroxyl protective group, reacting with a trifluoro- or trichloroacetimidate of a 2,3,4,6-tetraacylated D-glucose and eliminating the O-acyl groups. When a D,L-ceramide (II) is used, the esterification of the 3-hydroxyl group is carried out with an optically active acid, followed by separation into the diastereomers, or a separation into the diastereomers is carried out after the reaction with the D-glucose derivative.

Inventors

• 👤 Roland Dr. Tschannen
• 👤 Wolfgang Prof. Dr. Fraefel
• 👤 Richard R. Prof. Dr. Schmidt
• 👤 Rudolf Kläger
• 👤 Peter Zimmermann

Bibliographic Details