Biologically active glycosides from asteroidea, XXIV. Stereochemistry of the four diastereomers of phytosphingosine

Abstract

Abstract Diastereomeric D ‐ ribo ‐(2 S ,3 S ,4 R )‐, D ‐ lyxo ‐(2 S ,3 S ,4 S )‐, D ‐ arabino ‐(2 S ,3 R ,4 S )‐, and D ‐ xylo ‐(2 S ,3 R ,4 R )‐C 16 ‐phytosphingosine tetraacetates 2 – 5 were synthesized from the oxazoline 11 derived from ( S )‐serine. Detailed physical data were obtained and the stereochemistry can be readily identified, regardless of any new phytosphingosine moiety of the glucosphingolipids which may be detected in nature.