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• W3198996924 startingPage "25397" @default.
• W3198996924 abstract "Low-temperature NMR studies with a 4-C-methyl-4-O-benzoyl galactopyranosyl donor enable the observation and characterization of a bridged bicyclic dioxacarbenium ion arising from participation by a distal ester. Variable-temperature NMR studies reveal this bridged ion to decompose at temperatures above ≈−30 °C. In the absence of the methyl group, the formation of a bicyclic ion is not observed. It is concluded that participation by typical secondary distal esters in glycosylation reactions is disfavored in the ground state conformation of the ester from which it is stereoelectronically impossible. Methylation converts the secondary ester to a conformationally more labile tertiary ester, removes this barrier, and renders participation more favorable. Nevertheless, the minor changes in selectivity in model glycosylation reactions on going from the secondary to the tertiary esters at both low and room temperature argue against distal group participation being a major stereodirecting factor even for the tertiary system." @default.
• W3198996924 created "2021-09-27" @default.
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• W3198996924 date "2021-10-21" @default.
• W3198996924 modified "2023-10-02" @default.
• W3198996924 title "Direct Experimental Characterization of a Bridged Bicyclic Glycosyl Dioxacarbenium Ion by ¹ H and ¹³ C NMR Spectroscopy: Importance of Conformation on Participation by Distal Esters" @default.
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• W3198996924 doi "https://doi.org/10.1002/anie.202110212" @default.
• W3198996924 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/8595841" @default.
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• W3198996924 hasPublicationYear "2021" @default.
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