ArticleAngewandte Chemie (International ed. in English)2020
Remote Participation during Glycosylation Reactions of Galactose Building Blocks: Direct Evidence from Cryogenic Vibrational Spectroscopy.
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 54 papers.
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Who cites it
54 citing papers in PubMed, 115 citations in OpenAlex.
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- Steroid Fingerprinting with Cryogenic Gas-Phase Infrared Spectroscopy.ACS measurement science au · 2026Article
- Beyond the two-conformer model: boat conformers provide stereoselectivity in SChemical science · 2026Article
- 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
- Stereoselective Ferrier-Type O-Glycosylation Enabled by Difluoromethylated Glycal Donors.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
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- How to Use Quantum Chemistry for Analyzing Mass Spectrometry Data.Mass spectrometry (Tokyo, Japan) · 2026Review
- Total Synthesis and Anomeric Configuration Revision of Zwitterionic Polysaccharide A2's Pentasaccharide Repeating Unit fromJACS Au · 2025Article
- Mechanism of 3-The Journal of organic chemistry · 2025Article
- Distinguishing Isomeric Caffeine Metabolites through Protomers and Tautomers Using Cryogenic Gas-Phase Infrared Spectroscopy.Analytical chemistry · 2025Article
- Acceptor-Adaptive Automated Glycosylation Optimization for Automated Glycan Assembly.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Automated Glycan Assembly ofJournal of the American Chemical Society · 2025Article
- Carbohydrate Synthesis is Entering the Data-Driven Digital Era.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Elucidating reactive sugar-intermediates by mass spectrometry.Communications chemistry · 2025Review
- Mechanism of C-3 Acyl Neighboring Group Participation in Mannuronic Acid Glycosyl Donors.Journal of the American Chemical Society · 2025Article
- Stereoelectronic Effect of Protecting Groups on the Stability of Galactosyl Donor Intermediates.Molecules (Basel, Switzerland) · 2025Article
- The effect of neighbouring group participation and possible long range remote group participation inBeilstein journal of organic chemistry · 2025Review
Corrections and comments
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Authors and funding
12 authors at 3 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The stereoselective formation of 1,2-cis-glycosidic bonds is challenging. However, 1,2-cis-selectivity can be induced by remote participation of C4 or C6 ester groups. Reactions involving remote participation are believed to proceed via a key ionic intermediate, the glycosyl cation. Although mechanistic pathways were postulated many years ago, the structure of the reaction intermediates remained elusive owing to their short-lived nature. Herein, we unravel the structure of glycosyl cations involved in remote participation reactions via cryogenic vibrational spectroscopy and first principles theory. Acetyl groups at C4 ensure α-selective galactosylations by forming a covalent bond to the anomeric carbon in dioxolenium-type ions. Unexpectedly, also benzyl ether protecting groups can engage in remote participation and promote the stereoselective formation of 1,2-cis-glycosidic bonds.
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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.