Original scientific paper

Studies in the Sphingolipids Series. V. Synthesis of Racemic Dihydrosphingosine Derivatives Starting with DL-Serine

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

Abstract

Derivatives of racemic dihydrosphingosine were obtained by condensation of diibenzyl sodiotetradecylmalonate [II] with DL-aphthaloylamino-B-ethoxypropionic acid chloride [III]. Following new compounds are described: 1. 1-ethoxy-2-phthaloylamino-3-octadecanone [VJ, m. ;p. 4~40.5°; 2. 1-ethoxy-2-(N-isoindolinyl-)3-hydroxyoctadecane [VI], m. p. 59-60°; 3. 1-ethoxy-2-phthaloylamino-3-hydroxyoctadecane [VII], m. p. 80-81° . It has been shown in this manner that DL-serine can also be used as starting material in the in vitro formation of the C18-chain of sphingosine bases. A convenient preparation of DL-a-phthaloylamino-B-ethoxypropionic acid and of its chloride [III] is given.

Keywords

Hrčak ID:

247907

URI

https://hrcak.srce.hr/247907

Publication date:

1.2.1956.

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