ArticleEuropean journal of organic chemistry2022
Neighboring Group Participation of Benzoyl Protecting Groups in C3- and C6-Fluorinated Glucose.
Article in European journal of organic chemistry, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
13 citing papers in PubMed, 23 citations in OpenAlex.
- Beyond the two-conformer model: boat conformers provide stereoselectivity in SChemical science · 2026Article
- Evaluating Participation Modes in Peracetylated Glycosyl Cations.Organic letters · 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
- Stereoelectronic Effect of Protecting Groups on the Stability of Galactosyl Donor Intermediates.Molecules (Basel, Switzerland) · 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
- Decoding the Fucose Migration Product during Mass-Spectrometric analysis of Blood Group Epitopes.Angewandte Chemie (International ed. in English) · 2023Article
- Characterization and Fate of a Septanosyl Ferrier Cation in the Gas and Solution Phases.The Journal of organic chemistry · 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
- Emerging scientists in analytical sciences: Kim Greis.Analytical science advances · 2022Article
- Neighboring Group Participation of Benzoyl Protecting Groups in C3- and C6-Fluorinated Glucose.European journal of organic chemistry · 2022Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
10 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Fluorination is a potent method to modulate chemical properties of glycans. Here, we study how C3- and C6-fluorination of glucosyl building blocks influence the structure of the intermediate of the glycosylation reaction, the glycosyl cation. Using a combination of gas-phase infrared spectroscopy and first-principles theory, glycosyl cations generated from fluorinated and non-fluorinated monosaccharides are structurally characterized. The results indicate that neighboring group participation of the C2-benzoyl protecting group is the dominant structural motif for all building blocks, correlating with the β-selectivity observed in glycosylation reactions. The infrared signatures indicate that participation of the benzoyl group in enhanced by resonance effects. Participation of remote acyl groups such as Fmoc or benzyl on the other hand is unfavored. The introduction of the less bulky fluorine leads to a change in the conformation of the ring pucker, whereas the structure of the active dioxolenium site remains unchanged.
Indexed as
Identifiers
What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.