ArticleJournal of the American Chemical Society2019
Matching Glycosyl Donor Reactivity to Sulfonate Leaving Group Ability Permits S
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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Who cites it
23 citing papers in PubMed.
- Stereoselectivity of Galactosylation Reactions In Vacuo.Journal of the American Chemical Society · 2026Article
- Carbene-catalyzed site-selective sulfonylation and modular edition of monosaccharides for hydroxyl group stereoinversion and swapping.Nature communications · 2026Article
- Stereospecific Synthesis of 2-Deoxy-2-fluoroglycosides via SCCS chemistry · 2026Article
- Development, Scope, and Catalyst Selection in Boron-Catalyzed Iterative Glycosylation.Journal of the American Chemical Society · 2025Article
- Stereoselective Approaches to β-Linked 2-Deoxy Sugars.Molecules (Basel, Switzerland) · 2025Review
- Elucidating reactive sugar-intermediates by mass spectrometry.Communications chemistry · 2025Review
- The Stereoselectivity of Neighboring Group-Directed Glycosylation Is Concentration-Dependent.Journal of the American Chemical Society · 2025Article
- Structural analysis of stereoselective galactose pyruvylation toward the synthesis of bacterial capsular polysaccharides.Beilstein journal of organic chemistry · 2025Article
- Stereoselective Conversions of Carbohydrate Anomeric Hydroxyl Group in Basic and Neutral Conditions.Molecules (Basel, Switzerland) · 2024Review
- Stereoselective chemical N-glycoconjugation of amines via CONature communications · 2024Article
- Development of a Cryogenic Flow Reactor to Optimize Glycosylation Reactions Based on the Active Donor Intermediate.Organic process research & development · 2024Article
- Mechanistic insight into benzylidene-directed glycosylation reactions using cryogenic infrared spectroscopy.Nature synthesis · 2024Article
- Origins of Selectivity in Glycosylation Reactions with Saccharosamine Donors.Organic letters · 2023Article
- Unraveling the promoter effect and the roles of counterion exchange in glycosylation reaction.Science advances · 2023Article
- Hydrogen bond activated glycosylation under mild conditions.Chemical science · 2022Article
- Glycosyl Sulfonates Beyond Triflates.Chemical record (New York, N.Y.) · 2021Review
- Guidelines forACS central science · 2021Article
- Ab Initio Molecular Dynamics Simulations of the SJournal of the American Chemical Society · 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
- The Crossroads of Glycoscience, Infection, and Immunology.Frontiers in microbiology · 2021Article
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
Here we demonstrate that highly β-selective glycosylation reactions can be achieved when the electronics of a sulfonyl chloride activator and the reactivity of a glycosyl donor hemiacetal are matched. While these reactions are compatible with the acid- and base-sensitive protecting groups that are commonly used in oligosaccharide synthesis, these protecting groups are not relied upon to control selectivity. Instead, β-selectivity arises from the stereoinversion of an α-glycosyl arylsulfonate in an S
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