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Indium Bromide-catalyzed Unprecedented Hydrogenolysis: A Novel One-Pot Synthesis of Per-O-Acetylated β-carboxymethyl O and S-glycosides



Numerous O (oxa)- and S (thia)-glycosyl esters and their analogous glycosyl
acids have been accomplished through stereoselective glycosylation of various peracetylated
bromo sugar with benzyl glycolate using InBr3 as a glycosyl promotor followed
by in situ hydrogenolysis of resulting glycosyl ester. A tandem glycosylating and hydrogenolytic
activity of InBr3 has been successfully investigated in a one-pot procedure. The
resulting synthetically valuable and virtually unexplored class of β-CMGL (glycosyl acids)
could serve as an excellent potential chiral auxiliary in the asymmetric synthesis of a
wide range of enantiomerically pure medicinally prevalent β-lactams and other bioactive
molecules of diverse medicinal interest.
