ArticleAngewandte Chemie (International ed. in English)2022
Characterization of Mannosyl Dioxanium Ions in Solution Using Chemical Exchange Saturation Transfer NMR Spectroscopy.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed.
- Chemical exchange saturation transfer NMR: An analytical tool and its applications.Magnetic resonance letters · 2026Review
- Evaluating Participation Modes in Peracetylated Glycosyl Cations.Organic letters · 2026Article
- Elucidating the Stereodirecting Effect of C-4 Acyl Groups on Galactosyl Donors.Angewandte Chemie (International ed. in English) · 2026Article
- Detecting glycosyl-oxonium and glycosyl-nitrilium ions using exchange NMR to investigate solvent effects in glycosylation reactions.Nature communications · 2026Article
- Mechanism of 3-The Journal of organic chemistry · 2025Article
- Elucidating the Curtin-Hammett Principle in Glycosylation Reactions: The Decisive Role of Equatorial Glycosyl Triflates.Journal of the American Chemical Society · 2025Article
- Mechanism of C-3 Acyl Neighboring Group Participation in Mannuronic Acid Glycosyl Donors.Journal of the American Chemical Society · 2025Article
- The effect of neighbouring group participation and possible long range remote group participation inBeilstein journal of organic chemistry · 2025Review
- Anomeric Triflates versus Dioxanium Ions: Different Product-Forming Intermediates from 3-Acyl Benzylidene Mannosyl and Glucosyl Donors.The Journal of organic chemistry · 2024Article
- Detection and Characterization of Rapidly Equilibrating Glycosylation Reaction Intermediates Using Exchange NMR.Journal of the American Chemical Society · 2023Article
- Unraveling the promoter effect and the roles of counterion exchange in glycosylation reaction.Science advances · 2023Article
- Competing C-4 and C-5-Acyl Stabilization of Uronic Acid Glycosyl Cations.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- The Influence of the Electron Density in Acyl Protecting Groups on the Selectivity of Galactose Formation.Journal of the American Chemical Society · 2022Article
- Stabilization of Glucosyl Dioxolenium Ions by "Dual Participation" of the 2,2-Dimethyl-2-(The Journal of organic chemistry · 2022Article
- Characterization of Elusive Reaction Intermediates Using Infrared Ion Spectroscopy: Application to the Experimental Characterization of Glycosyl Cations.Accounts of chemical research · 2022Review
- Influence of 3-Thio Substituents on Benzylidene-Directed Mannosylation. Isolation of a Bridged Pyridinium Ion and Effects of 3-European journal of organic chemistry · 2022Article
- Characterization of Mannosyl Dioxanium Ions in Solution Using Chemical Exchange Saturation Transfer NMR Spectroscopy.Angewandte Chemie (International ed. in English) · 2022Article
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5 authors.
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Abstract
The stereoselective introduction of the glycosidic bond remains one of the main challenges in carbohydrate synthesis. Characterizing the reactive intermediates of this reaction is key to develop stereoselective glycosylation reactions. Herein we report the characterization of low-populated, rapidly equilibrating mannosyl dioxanium ions that arise from participation of a C-3 acyl group using chemical exchange saturation transfer (CEST) NMR spectroscopy. Dioxanium ion structure and equilibration kinetics were measured under relevant glycosylation conditions and highly α-selective couplings were observed suggesting glycosylation took place via this elusive intermediate.
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