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 regioselective derivatization of all functional groups of 1 is also reported....

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Bibliographic Details
Published in:Journal of organic chemistry 2001-09, Vol.66 (19), p.6209-6216
Main Authors: Bernardi, Anna, Arosio, Daniela, Manzoni, Leonardo, Micheli, Fabrizio, Pasquarello, Alessandra, Seneci, Pierfausto
Format: Article
Language:English
Subjects:
Cyclohexanols - chemical synthesis
Cyclohexanols - chemistry
Drug Design
Molecular Conformation
Molecular Mimicry
Monosaccharides - chemical synthesis
Monosaccharides - chemistry
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo015570b