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• W4289076536 abstract "Some terpenyl 2,3,4-tri-O-acetyl-α-D-glucuronide methyl esters were facilely synthesized from commercially available methyl 1,2,3,4-tetra-O-acetyl-β-D-glucuronate and terpenoid alcohols in the presence of bis(trifluoromethanesulfonyl)imide (Tf2NH) in dichloromethane (DCM) in good yields. The predominant α-selectivity at the anomer position is caused via transition state in which the neighboring group participation of the methoxycarbonyl group at C-6 stabilizes the oxonium intermediate by forming 1C4 conformation. The intermediate accelerates the glucuronidation reaction despite the use of the acetyl group, which is not a good activating group in general glycosylation reactions, as the activating group." @default.
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• W4289076536 date "2022-08-01" @default.
• W4289076536 modified "2023-10-03" @default.
• W4289076536 title "A Facile α-Glucuronidation Using Methyl 1,2,3,4-Tetra-<i>O</i>-acetyl-D-glucuronate as Glycosyl Donor" @default.
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• W4289076536 doi "https://doi.org/10.1248/cpb.c22-00123" @default.
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