Synthesis and glycosidase inhibition of new enantiopure 2,3-diamino conduritols

A new 2,3-diamino conduritol, isoster of conduritol F, was obtained starting from d-sorbitol. In the synthetic sequence an unprecedented transannular cyclization led, as a side product, to a bicyclic compound bearing a cyclopropyl ring. The synthesis of the completely deprotected 2,3-diamino conduritol, isoster of conduritol B, was devised via the intermediate O-benzylation of the OH groups. The O-methylated and deprotected 2,3-diamino conduritols were evaluated as inhibitors of α- and β-glucosidase.