ArticleChemistry (Weinheim an der Bergstrasse, Germany)2022
Competing C-4 and C-5-Acyl Stabilization of Uronic Acid Glycosyl Cations.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed, 20 citations in OpenAlex.
- Elucidating the Stereodirecting Effect of C-4 Acyl Groups on Galactosyl Donors.Angewandte Chemie (International ed. in English) · 2026Article
- Elucidating reactive sugar-intermediates by mass spectrometry.Communications chemistry · 2025Review
- Neighboring-Group Participation by a Less Electron-Donating, Participating C-2-Ester Ensures Higher 1,2-The Journal of organic chemistry · 2025Article
- Mechanism of C-3 Acyl Neighboring Group Participation in Mannuronic Acid Glycosyl Donors.Journal of the American Chemical Society · 2025Article
- Anomeric Triflates versus Dioxanium Ions: Different Product-Forming Intermediates from 3-Acyl Benzylidene Mannosyl and Glucosyl Donors.The Journal of organic chemistry · 2024Article
- Mechanistic insight into benzylidene-directed glycosylation reactions using cryogenic infrared spectroscopy.Nature synthesis · 2024Article
- Detection and Characterization of Rapidly Equilibrating Glycosylation Reaction Intermediates Using Exchange NMR.Journal of the American Chemical Society · 2023Article
- Neighboring-Group Participation by C-2 Acyloxy Groups: Influence of the Nucleophile and Acyl Group on the Stereochemical Outcome of Acetal Substitution Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 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
Corrections and comments
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Authors and funding
11 authors at 2 institutions in 2 countries.
Funding
Abstract
Uronic acids are carbohydrates carrying a terminal carboxylic acid and have a unique reactivity in stereoselective glycosylation reactions. Herein, the competing intramolecular stabilization of uronic acid cations by the C-5 carboxylic acid or the C-4 acetyl group was studied with infrared ion spectroscopy (IRIS). IRIS reveals that a mixture of bridged ions is formed, in which the mixture is driven towards the C-1,C-5 dioxolanium ion when the C-5,C-2-relationship is cis, and towards the formation of the C-1,C-4 dioxepanium ion when this relation is trans. Isomer-population analysis and interconversion barrier computations show that the two bridged structures are not in dynamic equilibrium and that their ratio parallels the density functional theory computed stability of the structures. These studies reveal how the intrinsic interplay of the different functional groups influences the formation of the different regioisomeric products.
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