Process for the preparation of sphingosine derivatives

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

1986-08-11

1990-06-26

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

049373285

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.

REFERENCES:
patent: 4415733 (1983-11-01), Tayot
Schmidt et al., Angew Chem. 94, 215-216 (1982).
Angew. Chem. Int. Ed. Engl. 21, 210-211 (1982).
Angew. Chem. Suppl. 1982, 393-397.
Reist et al., J. Org. Chem. 35, 3521-3524 (1970).
Newman, J. Am. Chem. Soc. 95, 4098-4099 (1973).
Tkaczuk et al., J. Org. Chem. 46, 4393-4398 (1981).
Bernet et al., Tetrahedron Letters 24, 5491-5494 (1983).
Koike et al., Glycoconjugate J. 1, 107-109 (1984).

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