Glycosyl halides that have been utilized in glycosylation since the early studies by Michael, Koenigs/Knorr, and Fischer remain prominent glycosyl donors. Many efforts to improve the outcome of reactions with glycosyl halides have emerged. The key emphasis has traditionally been placed on reaction rates, product yields, and stereocontrol.  Recently, we reported that silver(I) oxide mediated Koenigs-Knorr glycosylation reaction can be dramatically accelerated in the presence of catalytic acid additives. We have also investigated how well this reaction works in application to differentially protected galactosyl bromides.  Reported herein is the development of a highly stereocontrolled alpha-galactosylation reaction with glycosyl chlorides as donors. Chlorides are easily accessible, stable, and can be efficiently activated for glycosylation. The initial steps dedicated to the refinement of the basic reaction conditions evolved into showcasing our methodology in application to iterative synthesis of 1,2-<i>cis</i>-linked galactooligosaccharides.

Defining the scope of the stereocontrolled α-galactosylation under cooperative catalysis

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ACS Fall 2022

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