Stereoselective synthesis of conformationally constrained cyclohexanediols: A set of molecular scaffolds for the synthesis of glycomimetics

The practical, stereoselective synthesis of the three diastereoisomeric 1,2 -trans-dicarboxy-4,5-cyclohexanediols. 1-3 (DCCHDs) is described, starting from a common precursor, easily available in both enantiomeric forms. The r egioselective derivatization of all functional groups of I is also reported . The three DCCHDs are locked in a single chair conformation and thus can b e used to mimic vicinally disubstituted monosaccharides of any relative con figuration.