Macrocyclic bis-thioureas catalyze stereospecific glycosylation reactions
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CitationPark, Yongho, Kaid C. Harper, Nadine Kuhl, Eugene E. Kwan, Richard Y. Liu, and Eric N. Jacobsen. "Macrocyclic Bis-thioureas Catalyze Stereospecific Glycosylation Reactions." Science 355, no. 6321 (2017): 162-166.
AbstractCarbohydrates are involved in nearly all aspects of biochemistry, but their complex chemical structures present long-standing practical challenges to their synthesis. In particular, stereochemical outcomes in glycosylation reactions are highly dependent on the steric and electronic properties of coupling partners; thus, carbohydrate synthesis is not easily predictable. Here we report the discovery of a macrocyclic bis-thiourea derivative that catalyzes stereospecific invertive substitution pathways of glycosyl chlorides. The utility of the catalyst is demonstrated in the synthesis of trans-1,2-, cis-1,2-, and 2-deoxy-β-glycosides. Mechanistic studies are consistent with a cooperative mechanism in which an electrophile and a nucleophile are simultaneously activated to effect a stereospecific substitution reaction.
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