Solco Basel Ag

Rudolf Klager

Richard R Schmidt

Wolfgang Fraefel

Roland Tschannen

Peter Zimmermann

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.

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Eutingen, Germany

Rudolf Klager