A Stereoselective Synthesis of an Imino Glycal: Application in the Synthesis of (-)-1-epi-Adenophorine and a Homoimindosugar

A concise stereoselective synthesis of an imino glycal is described in 8 steps starting from 1,2-anhydro-3,4,6-tri-O-benzyl-d-glucopyranose. The utility of the imino glycal has been demonstrated in synthesis of (-)-1-epi-adenophorine and a homoiminosugar as a glycosidase inhibitor. The important features of the developed route include high yields, high stereoselectivity, and application in the synthesis of other iminosugars. Additionally, a new synthon 2-nitro-imino glycal has also been synthesized which could act as valuable synthon in carbohydrate chemistry.