Synthesis of galactosylphytosphingosine and galactosylceramides containing phytosphingosine

✍ Scribed by Irmin Pascher

• Book ID: 103040712
• Publisher: Elsevier Science
• Year: 1974
• Tongue: English
• Weight: 760 KB
• Volume: 12
• Category: Article
• ISSN: 0009-3084
• DOI: 10.1016/0009-3084(74)90057-7

✦ Synopsis

Phytosphingosine prepared from the yeast Hansenula ciferrff 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 ~-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.