Method of preparing sphingosine derivatives

Details Method of preparing sphingosine derivatives Method of preparing sphingosine derivatives

1988-06-17

1992-05-05

Wax, Robert A.

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

Organic compounds

Amino nitrogen containing

564304, 564487, C07C20954

Patent

active

051109875

ABSTRACT:
A method of preparing a substituted derivative of sphingosine comprising the steps of reducing serine methyl ester by a hydride reagent to form an aldehyde or aldehyde derivative, adding acetylide anions to the aldehyde to form an erythro-isomer or propargyl alcohol and inverting the propargyl alcohol by S.sub.N 2 inversion to form a threo-isomer. Either isomer can then be deprotected to form an alkyne with a 2-aminopropane 1,3-diol head group; this alkyne can be reduced to form sphingosine or a sphingosine derivitive which can be functionalized at the 4 and 5 positions to form a substituted derivative of sphingosine.

REFERENCES:
patent: 2194294 (1940-03-01), Cass
patent: 4463192 (1984-07-01), Duranleau
CA) 109:110149g of Garner et al. J. Org. Chem 1988, 53(18) 4395-8.
CA) 109:230620a of Herold Helv. Chim. Acta 1988, 71(2) 354-62.
CA) 110:7935g of Radunz et al. Liebigs Ann. Chem 1988, (11), 1103-5.

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