ArticleThe Journal of organic chemistry2008
Installation of electron-donating protective groups, a strategy for glycosylating unreactive thioglycosyl acceptors using the preactivation-based glycosylation method.
Article in The Journal of organic chemistry, 2008. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 37 papers.
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Who cites it
37 citing papers in PubMed.
- Iron-Catalyzed Highly Stereospecific Glycosylation with Glycal Epoxides.Angewandte Chemie (International ed. in English) · 2025Article
- Article
- The Stereoselectivity of Neighboring Group-Directed Glycosylation Is Concentration-Dependent.Journal of the American Chemical Society · 2025Article
- Neighboring-Group Participation by a Less Electron-Donating, Participating C-2-Ester Ensures Higher 1,2-The Journal of organic chemistry · 2025Article
- Structural analysis of stereoselective galactose pyruvylation toward the synthesis of bacterial capsular polysaccharides.Beilstein journal of organic chemistry · 2025Article
- Unraveling the promoter effect and the roles of counterion exchange in glycosylation reaction.Science advances · 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
- Synthesis and biological activity of ganglioside GM3 analogues with a (S)-CHF-Sialoside linkage and an alkyne tag.Glycoconjugate journal · 2023Article
- Involvement of an Oxonium Ion Intermediate in Controlling the Diastereoselectivity of Nucleophilic Substitution Reactions of Septanoses.Organic letters · 2023Article
- The Influence of the Electron Density in Acyl Protecting Groups on the Selectivity of Galactose Formation.Journal of the American Chemical Society · 2022Article
- Halogen Atom Participation in Guiding the Stereochemical Outcomes of Acetal Substitution Reactions.Angewandte Chemie (International ed. in English) · 2022Article
- Visible-Light-Mediated Stadler-Ziegler Arylation of Thiosugars with Anilines.ACS organic & inorganic Au · 2022Article
- Characterization of Mannosyl Dioxanium Ions in Solution Using Chemical Exchange Saturation Transfer NMR Spectroscopy.Angewandte Chemie (International ed. in English) · 2022Article
- Direct Experimental Characterization of a Bridged Bicyclic Glycosyl Dioxacarbenium Ion byAngewandte Chemie (International ed. in English) · 2021Article
- Transition-metal-free synthesis of aryl 1-thioglycosides with arynes at room temperature.RSC advances · 2021Article
- Long-Range Stereodirecting Participation across a Glycosidic Linkage in Glycosylation Reactions.Organic letters · 2021Article
- En Route to the Transformation of Glycoscience: A Chemist's Perspective on Internal and External Crossroads in Glycochemistry.Journal of the American Chemical Society · 2021Article
- A Streamlined Regenerative Glycosylation Reaction: Direct, Acid-Free Activation of Thioglycosides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Mechanisms of Stereodirecting Participation and Ester Migration from Near and Far in Glycosylation and Related Reactions.Chemical reviews · 2020Article
- Chemical synthesis of human syndecan-4 glycopeptide bearing O-, N-sulfation and multiple aspartic acids for probing impacts of the glycan chain and the core peptide on biological functions.Chemical science · 2020Article
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4 authors.
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Abstract
Preactivation-based chemoselective glycosylation is a powerful strategy for oligosaccharide synthesis with its successful application in assemblies of many complex oligosaccharides. However, difficulties were encountered in reactions where glycosyl donors bearing multiple electron-withdrawing groups failed to glycosylate hindered unreactive acceptors. In order to overcome this problem, it was discovered that the introduction of electron-donating protective groups onto the glycosyl donors can considerably enhance their glycosylating power, leading to productive glycosylations even with unreactive acceptors. This observation is quite general and can be extended to a wide range of glycosylation reactions, including one-pot syntheses of chondroitin and heparin trisaccharides. The structures of the reactive intermediates formed upon preactivation were determined through low-temperature NMR studies. It was found that for a donor with multiple electron-withdrawing groups, the glycosyl triflate was formed following preactivation, while the dioxalenium ion was the major intermediate with a donor bearing electron-donating protective groups. As donors were all cleanly preactivated prior to the addition of the acceptors, the observed reactivity difference between these donors was not due to selective activation encountered in the traditional armed-disarmed strategy. Rather, it was rationalized by the inherent internal energy difference between the reactive intermediates and associated oxacarbenium ion like transition states during nucleophilic attack by the acceptor.
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