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

Stereoselective synthesis of conformationally constrained cyclohexanediols: a set of molecular scaffolds for the synthesis of glycomimetics / A. Bernardi, D. Arosio, L. Manzoni, F. Micheli, A. Pasquarello, P. Seneci. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 66:19(2001 Sep 21), pp. 6209-6216.

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

A. Bernardi
Primo
;
P. Seneci
Ultimo
2001

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
Molecular Mimicry ; Molecular Conformation ; Cyclohexanols ; Drug Design ; Monosaccharides
Settore CHIM/06 - Chimica Organica
21-set-2001
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/170560
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