Stereoselective synthesis of conformationally constrained cyclohexanediols: a set of molecular scaffolds for the synthesis of glycomimetics |
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Authors: | Bernardi A Arosio D Manzoni L Micheli F Pasquarello A Seneci P |
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Institution: | Universita' di Milano, Dipartimento di Chimica Organica e Industriale, via Venezian 21, 20133 Milano, Italy. anna.bernardi@unimi.it |
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Abstract: | 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 regioselective derivatization of all functional groups of 1 is also reported. The three DCCHDs are locked in a single chair conformation and thus can be used to mimic vicinally disubstituted monosaccharides of any relative configuration. |
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