A synthesis of L-ribo-2-amino-1,3,4-trihydroxyeicosane from D-galactose

Abstract

L-arabino-1,2,3,4-Tetrahydroxyeicosane was synthesised by catalytic reduction of the product obtained from a Wittig reaction between the phosphorane derived from n-pentadecyltriphenylphosphonium bromide, and 2,3,4,5-tetra-O-benzylaldehydo-L-lyxose. The tetrahydroxyeicosane was coverted via the triphenylmethyl ether of L-ribo-2-azido-3,4-dibenzyloxy-1-hydroxyeicosane into the title compound, which is the enantiomer of C20-phytosphingosine.