Chemoenzymatic synthesis of the carbasugars carba-β-l-galactopyranose, carba-β-l-talopyranose and carba-α-l-talopyranose from methyl benzoate

Abstract

The cis-dihydrodiol metabolite from methyl benzoate has been used as a synthetic precursor of carba-β-L-galactopyranose, carba-β-L-talopyranose and carba-α-L-talopyranose. The structures and absolute configurations of these carbasugars were determined by a combination of NMR spectroscopy, stereochemical correlation and X-ray crystallography.