The synthesis of (2S,3R)-sphingose from D-mannitol

(2E)-4,5-O-Isopropylidene-pentenylic ester (5), obtained in 3 steps from D-mannitol, was subjected to a series of reactions such as asymmetric dihydroxidation, cyclic sulfation and regioselective opening of the cyclic sulfate by NaN3 and finally was transformed into the 2,3-dibenzoate of (2S,3R)-sphingosine. The overall yield from D-mannitol was 7.7%. This work has opened a new route to thr synthesis of sphingosine and other sphingolipids.