A short and practical route to 3-O-benzoyl azidosphingosine

A short and practical route to 3-O-benzoyl azidosphingosine from d-xylose is described. The synthesis avoids the use of expensive and hazardous chemicals (i.e. mercury salts), and it is reproducible up to at least a 20 g scale. Furthermore, the synthesis proceeds to 3-O-benzoyl azidosphingosine with a minimum of protection group manipulation, by exploiting a regioselective protection of the primary HO-1 with thexyldimethylsilyl chloride.