Process for the synthesis of sphingosine

Details Process for the synthesis of sphingosine Process for the synthesis of sphingosine

2005-02-08

2005-02-08

Davis, Brian J. (Department: 1621)

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

Organic compounds

Amino nitrogen containing

C564S468000, C564S507000, C564S509000

Reexamination Certificate

active

06852892

ABSTRACT:
This invention relates to a method for the production of a sphingoid base according to formulacomprising the steps of(1) dissolving a starting compound according to formula III or a salt thereof in a substantially inert solvent,(2) protecting the NH2group with a NH2protecting group,(3) activating the C-4 HR3group for an elimination reaction with the C-5 HR4group,(4) causing an elimination reaction to take place to form a double bond between the C-4 and C-5 carbon atom, and(5) removing the NH2protecting group.

REFERENCES:
patent: WO 9512683 (1995-05-01), None
Shapiro, David and Khyaim Segal. “The Synthesis of Sphingosine”, J. Amer. Chem. Soc. (1954), vol. 76, p 5894-5.
Wild, Robert and Richard R. Schmidt. “Sphingosine and Phytosphingosine from D-Threose Synthesis of a 4-Keto-Ceramide”, Tetrahedron: Asymmetry, vol. 5 No. 11, pp. 2195-2208, 1994.
Koskinen, Paivi M. and Ari M.P. Koskinen. “Sphingosine, and Enigmatic Lipid: A Review of Recent Literature Syntheses”, Synthesis, vol. 8, p 1075-1091.
Gargano, Joseph M. and Watson J. Lees. “Synthesis of an orthogonally protected D-(+)-erythro-sphingosine”, Tetrahedron Letters 42 (2001), pp. 5845-5847.
Compostella, Federica, Laura Franchini, Luigi Panza, Davide Prosperi and Fiamma Ronchetti. “A formal synthesis of 3-0-4-(4-methoxybenzyl)-azidosphingosine by a modified Julia olefination”, Tetrahedron 58 (2002). Italy, Apr. 11, 2002.

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