Process for the preparation of sphingosine derivatives

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

1987-12-24

1990-08-28

Brown, Johnnie R.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 179, 536 185, C07H 506

Patent

active

049526839

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.

REFERENCES:
patent: 4042538 (1977-08-01), Lucas
patent: 4362720 (1982-12-01), Lemieux et al.
Jungerman et al., Biochemie pp. 448, 1980, published by Springer-Verlag Berlin, Heidelburg, N.Y.
Lehringer, Biochemie pp. 177-180, 1975, published by Verlag-Chemie.
Schmidt et al., Chemical Abstracts, vol. 96, (1982), No. 123 141m.

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