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. The three DCCHDs are locked in a single chair conformation and thus can be used to mimic vicinally disubstituted monosaccharides of any relative configuration.
Bernardi
A
A
Universita' di Milano, Dipartimento di Chimica Organica e Industriale, via Venezian 21, 20133 Milano, Italy. anna.bernardi@unimi.it
Arosio
D
D
Manzoni
L
L
Micheli
F
F
Pasquarello
A
A
Seneci
P
P
D003511:Cyclohexanols / Q000138:chemical synthesis* / Q000737:chemistry*; D015195:Drug Design; D008968:Molecular Conformation; D018716:Molecular Mimicry; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*
D003511:Cyclohexanols; D009005:Monosaccharides