I. Pascher
Jul 1, 1974
Citations
0
Influential Citations
23
Citations
Journal
Chemistry and physics of lipids
Abstract
Abstract Phytosphingosine prepared from the yeast Hansenula ciferrii was used for synthesis of galactosphingolipids. Glycosidation of N -dichloroacetyl and 3,4-di- O -benzoyl protected phytosphingosine was performed with acetobromogalactose in the presence of mercury cyanide. By subsequent alkaline hydrolysis of the protective groups 1- O ( β -D-galactopyranosyl)-phytosphingosine was obtained. The psychosine-like intermediate was N -acylated with p -nitrophenylesters of octadecanoic and 2D-hydroxyoctadecanoic acid to give cerebrosides. The overall yield for the synthesis was 30%. Melting points and optical rotation were recorded and the structures of the cerebrosides confirmed by infrared and mass spectra. The thin-layer chromatographic behaviour of corresponding synthetic sphingosine and phytosphingosine compounds was compared.