Partial Conversion of Maltose into Cyclohexane Derivatives

Abstract

5,6-Unsaturated disaccharide derivative prepared from maltose via its 6-iodo derivative was treated with mercuric chloride, giving α-linked pseudodisaccharide in good yield, which contains cyclohexanone derivatives as constituents. On treatment with an acetic anhydride-pyridine mixture, the cyclohexanone constituents underwent β-elimination to be changed into a sole cyclohexenone moiety. Hydrogenation of the double bond between two carbon atoms and subsequent reductive amination of the carbonyl group gave aminocyclitol-containing pseudodisaccharides.