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

Citation
A. Bernardi et al., Stereoselective synthesis of conformationally constrained cyclohexanediols: A set of molecular scaffolds for the synthesis of glycomimetics, J ORG CHEM, 66(19), 2001, pp. 6209-6216
Citations number
26
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
0022-3263 → ACNP
Volume
66
Issue
19
Year of publication
2001
Pages
6209 - 6216
Database
ISI
SICI code
0022-3263(20010921)66:19<6209:SSOCCC>2.0.ZU;2-I
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 r egioselective derivatization of all functional groups of I is also reported . The three DCCHDs are locked in a single chair conformation and thus can b e used to mimic vicinally disubstituted monosaccharides of any relative con figuration.