Efficient stereocontrolled synthesis of D-erythro-sphingosine from N-benzoyl-D-glucosamine

D-erythro-Sphingosine is synthesized from N-benzoyl-D-glucosamine 2 in a highly regio- and stereo-controlled manner; The key features in the synthesis involve the efficient conversion of compound 2 into the vinyl epoxide 10 and the subsequent S(N)2'-type reaction with a Grignard reagent in the presence of CuCN to afford the 1-O,2-N-protected sphingosine 11.