Synthesis of D-erythro-sphingomyelins

Details Synthesis of D-erythro-sphingomyelins Synthesis of D-erythro-sphingomyelins

1991-03-21

1993-06-15

Dees, Jose G.

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

Organic compounds

Fatty compounds having an acid moiety which contains the...

554 78, 554 79, 554 80, C07F 902

Patent

active

052200434

ABSTRACT:
A method for making optically pure D-erythro-sphingomyelins which may be labeled for identification and testing purposes is provided. The present method is directed to a five step synthesis comprising the steps of: (1) reacting a (2S,3R,4E)-2-azido-octadecen-1,3-diol composition having a protective functional group attached thereto with a solution of triphenylphosphine and water in a first solvent to form a protected sphingosine; (2) reacting a long-chain fatty acid with the protected sphingosine in the presence of N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline catalyst in a second solvent to form a protected ceramide; (3) reacting 2-chloro-2-oxo-1,3,2-dioxaphospholane with the protected ceramide in the presence of triethylamine and 4-dimethylaminopyridine catalyst in a third solvent to form a protected cyclic phosphotriester; (4) reacting trimethylamine with the protected cyclic phosphotriester in a solvent system to form a protected sphingomyelin; and (5) reacting tetra-n-butylammonium fluoride with the protected sphingomyelin in tetrahydrofuran to form the D-erythro-sphingomyelin composition.

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