Abstract
An efficient route for synthesizing bradyrhizose, a unique carbocyclic monosaccharide, as its methyl glycoside has been developed. The formation of the unusual 6-membered carbocyclic ring of bradyrhizose is constructed via the key intramolecular pinacol coupling of the keto aldehyde intermediate. The precursor was easily derived from the known appropriately protected d-glucose via chain elongation and Sharpless asymmetric dihydroxylation.
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