title: Stereoselective synthesis of conformationally constrained cyclohexanediols: a set of molecular scaffolds for the synthesis of glycomimetics.
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.
authors.affiliation: Universita' di Milano, Dipartimento di Chimica Organica e Industriale, via Venezian 21, 20133 Milano, Italy. anna.bernardi@unimi.it
authors.forename: A
authors.initials: A
authors.lastname: Bernardi
authors.forename: D
authors.initials: D
authors.lastname: Arosio
authors.forename: L
authors.initials: L
authors.lastname: Manzoni
authors.forename: F
authors.initials: F
authors.lastname: Micheli
authors.forename: A
authors.initials: A
authors.lastname: Pasquarello
authors.forename: P
authors.initials: P
authors.lastname: Seneci
mesh_terms: D003511:Cyclohexanols / Q000138:chemical synthesis* / Q000737:chemistry*; D015195:Drug Design; D008968:Molecular Conformation; D018716:Molecular Mimicry; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D003511:Cyclohexanols; D009005:Monosaccharides