Synthesis of 1,2-cis-HomoiminosugarsDerived from GlcNAc and GalNAc Exploiting a β-Amino AlcoholSkeletal Rearrangement.

The synthesis of 1,2-cis-homoiminosugars bearingan NHAc group at the C-2 position is described. The key step to preparethese α-d-GlcNAc and α-d-GalNAc mimicsutilizes a β-amino alcohol skeletal rearrangement applied toan azepane precursor. This strategy also allows access to naturallyoccurring α-HGJ and α-HNJ. The α-d-GlcNAc-configurediminosugar was coupled to a glucoside acceptor to yield a novel pseudodisaccharide.Preliminary glycosidase inhibition evaluation indicates that the α-d-GalNAc-configured homoiminosugar is a potent and selectiveα-N-acetylgalactosaminidase inhibitor. [ABSTRACT FROM AUTHOR]