An efficient, stereoselective synthesis of 4-E- and 4-Z-D-erythro-sphingenine and related compounds from 2-amino-2-deoxy-D-glucose.

Article abstract of DOI:10.1016/0008-6215(89)85012-8

Efficient, stereoselective synthesis of 4-E- and 4-Z-D-erythro-sphingenines having C16, C18, and C20 carbon-chains was achieved in 13 steps, starting from allyl 2-benzyloxycarbonylamino-2-deoxy-alpha-D-glucopyranoside. 2-Amino-1,6-di-O-tert- butyldiphenylsilyl-2-N,3-O-carbonyl-2-deoxy-D -allitol was used as the key intermediate.