Synthesis of 1,2-trans-2-Acetamido-2-deoxyhomoiminosugars

The first synthesis of 1,2-trans-homoiminosugars devised as mimics of beta-d-GlcNAc and a-d-ManNAc is described. Key steps include a regioselective azidolysis of a cyclic sulfite and a beta-amino alcohol skeletal rearrangement applied to a polyhydroxylated azepane. The beta-d-GlcNAc derivative has been coupled to serine to deliver an iminosugar C-amino acid. The two homoiminosugars demonstrate moderate glycosidase inhibition.