NOVEL SYNTHESIS INTERMEDIATES FOR OBTAINING DERIVATIVES OF SPHINGOSINES, CERAMIDES AND SPHINGOMYELINS WITH GOOD YIELDS

摘要

The subject matter of the present invention is the novel molecules of formulae E, E′ and F. These molecules prove to be synthesis intermediates that are very advantageous for the manufacture of derivatives of sphingosine or of ceramides functionalized in position 1, with good yields, in which R1 and R2 are fatty chains, R3 is an alkyl group and R4 is a protective group for alcohol functions. Another subject of the invention is the use of the intermediates of type F for converting same into intermediates of type G, by means of reduction in the presence of lithium borohydride. The G molecules are precursors that are known to make it possible to obtain sphingolipids or sphingomyelin.

主权项

1. Synthesis intermediates E, E′ and F to access derivatives of sphingosine or ceramides, of general formula: where: R1 is a saturated or unsaturated carbon fatty chain; R2 is an aliphatic fatty chain of general formula CnH2n+1, n being an integer greater than or equal to 8 and less than or equal to 35; R3 is a radical having at least 1 carbon atom of alkyl, aryl, alkyl-aryl type optionally substituted; R4 is a protective group of the alcohol functions and R4 is a benzyl, trityl, benzoyl, methoxymethyl, methoxyethyl, tetrahydropyryl, tri-alkyl silyl or alkyl-aryl silyl radical.