D-erythro-Sphingosine is synthesized from N-benzoyl-D-glucosamine 2 in a highly regio- and stereocontrolled manner. The key features in the synthesis involve the efficient conversion of compound 2 into the vinyl epoxide 10 and the subsequent SN2′-type reaction with a Grignard reagent in the presence of CuCN to afford the 1-O,2-N-protected sphingosine 11.
T. Murakami and M. Hato, J. Chem. Soc., Perkin Trans. 1, 1996, 823 DOI: 10.1039/P19960000823
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