A general, two-directional synthesis of C-(1→6)-linked disaccharide mimetics: synthesis from non-carbohydrate based starting materials

Abstract

The enantiomerically enriched diol 1,4-di(furan-2-yl)butane-1,4-diol (R,R)-1, synthesised either by Sharpless kinetic resolution or asymmetric reduction of the corresponding diketone, was a key intermediate in the stereodivergent synthesis of diastereoisomeric C-(1→6)-linked disaccharides. Two-directional stereoselective functionalisation steps, for example syn- and/or anti-selective dihydroxylation reactions, were exploited in the stereoselective synthesis of five diastereoisomeric C-linked disaccharides.