New azadisaccharide analogs as potential antidiabetics

The synthesis of various aminocyclitols displaying a N-substituted (or unsubstituted) polyhydroxycyclohexylamine structure is described. The strategy relies on two key steps: a tandem alkylation–cyclization of a C2-symmetrical bis-epoxide derived from d-mannitol and a reductive amination with several amines of the resulting polyhydroxycyclohexanone. Reduction of the latter also allows a rapid access to the corresponding carbasugars.