Asymmetric total syntheses of bioactive 1-azasugars

Carbohydrate-processing enzymes, such as glycosidases, are integral to cell and tissue function and have been implicated in a variety of metabolic disorders. Glycosidase inhibitors that are able to differentiate between enzymes may be powerful tools both in the study of glycosidase function and in the treatment of disease.;1-Azasugars are a novel class of saccharide mimics in which a nitrogen atom replaces the anomeric carbon. These compounds are potent, as well as anomer-specific glycosidase inhibitors.;An efficient, high-yielding approach to the synthesis of 1-azasugars from achiral starting materials has been developed. Short, asymmetric syntheses of isofagomine 12 and 3'-hydroxyisofagomine 15 are described herein. Additionally, the syntheses of novel 1-azasugars 70, 79 and 108, which may show biological activity, are presented.