A new simple route to deoxyamino sugars from non-sugar material: synthesis of d-tolyposamine and 4-epi-d-tolyposamine and formal synthesis of d-vicenisamine

A new, simple strategy has been formulated for the synthesis of deoxyamino sugars from a non-sugar starting material. Starting from the enantiomerically pure diol obtained from ethyl sorbate by Sharpless asymmetric dihydroxylation, the synthesis of two types of 2,3,4,6-tetradeoxy-4-amino sugars—d-tolyposamine and 4-epi-d-tolyposamine—, and formal synthesis of 2,4,6-trideoxy-4-amino sugar—d-vicenisamine—were performed.