Original scientific paper

Studies in the Sphingolipids Series. IX.* Synthesis of DL-2-Amino-1,3,4-trihydroxyoctadecane and of Its C4-Methyl Ether

N. Ž. Stanaćev ; Department of Chemistry, Faculty of Medicine, University of Zagreb and Department of Biochemistry, Institute »Ruder Boskovic«, Zagreb, Croatia, Yugoslavia
M. Proštenik ; Department of Chemistry, Faculty of Medicine, University of Zagreb and Department of Biochemistry, Institute »Ruder Boskovic«, Zagreb, Croatia, Yugoslavia

Abstract

DL-2 - Amino - 1,3,4 - trihydroxyoctadecane (IXa) and its C4 methyl ether (IXb) were prepared in a series of reactions through the following intermediates: 2-Methoxyhexdecanoic acid (III) --> Ethyl 2-methoxyhexadecanoylacetoacetate (IV) --> Ethyl (2-pnitrophenylhydrazono) -2,3-dioxo-4-methoxyoctadecanoate (V) --> Ethyl 2-acetamido-3-oxo-4-methoxyoctadecanoate (VI) --> Ethyl 2-acetamido-3-hydroxy-4-methoxyoctadecanoate (VII) --> 2-Amino- 3-hydroxyoctadecanoic acid 1,4-lactone (VIII) --> IX. The crude base mixture was precipitated with oxalic acid and the mixture of oxalates crystallized fractionally. Two oxalates of IXa were obtained probably representing two purified racemic forms. IXa was prepared as a free base. The N-benzoyl derivative of IXa was also prepared.

Keywords

Hrčak ID:

246481

URI

https://hrcak.srce.hr/246481

Publication date:

8.8.1957.

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