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

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 reducti on of the corresponding diketone, was a key intermediate in the stereodiver gent synthesis of diastereoisomeric C-(1 -->6)-linked disaccharides. Two-di rectional stereoselective functionalisation steps, for example syn- and/or anti-selective dihydroxylation reactions, were exploited in the stereoselec tive synthesis of five diastereoisomeric C-linked disaccharides.