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Creators/Authors contains: "Agarkar, Varad"

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  1. ; ; (, Journal of Carbohydrate Chemistry)
    Since no later than the 1970s, organic chemists have speculated on the role of glycosyl oxonium ions in chemical O-glycosylation. Such species result from the attack of ethers on glycosyl oxocarbenium ions and are invoked to explain 1,2-cis-selectivity in ether solvents. However, a systematic study to probe this phenomenon appears to be lacking in the chemical literature. Herein, we study the effects of solvent, counteranion, protecting group electron-withdrawing effects, and acceptor on O-glycosylation stereoselectivity with D-glucosyl trichloroacetimidate donors. While many of these transformations proceed with 1,2- cis-selectivity, our results suggest that glycosyl oxonium ions play minimal, if any, role in O-glycosylation. 
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    Free, publicly-accessible full text available November 21, 2025