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- W2951532745 abstract "The development of a new glycosylation method for the stereoselective synthesis of β-glycosides in the absence of the traditional C(2)-ester neighboring group effect is described. This process relies on the ability of the cationic palladium catalyst, Pd(PhCN)2(OTf)2 generated in situ from Pd(PhCN)2Cl2 and AgOTf, to direct β-selectivity. The new glycosylation reaction is highly β-selective and proceeds under mild conditions with 1−2 mol % of catalyst loading. This β-glycosylation method has been applied to a number of glucose donors with benzyl, allyl, and p-methoxybenzyl groups incorporated at the C(2)-position as well as tribenzylated xylose and quinovose donors to prepare various disaccharides and trisaccharides with good to excellent β-selectivity. Mechanistic studies suggest that the major operative pathway is likely to proceed via a seven-membered ring intermediate, wherein the cationic palladium complex coordinates to both the C(1)-imidate nitrogen and C(2)-oxygen of the trichloroacetimidate donor. Formation of this seven-membered ring intermediate directs the selectivity, leading to the formation of β-glycosides." @default.
- W2951532745 created "2019-06-27" @default.
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- W2951532745 date "2009-01-22" @default.
- W2951532745 modified "2023-09-25" @default.
- W2951532745 title "Palladium-Controlled β-Selective Glycosylation in the Absence of the C(2)-Ester Participatory Group" @default.
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- W2951532745 doi "https://doi.org/10.1021/jo802468p" @default.
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