ArticleScience (New York, N.Y.)2017
Macrocyclic bis-thioureas catalyze stereospecific glycosylation reactions.
Article in Science (New York, N.Y.), 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 112 papers.
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Who cites it
112 citing papers in PubMed, 306 citations in OpenAlex.
- AnilineScience advances · 2026Article
- Charting the Future of Stereoselective Carbohydrate Synthesis: The Essential Role of Cross-Disciplinary Innovation.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Carbene-catalyzed site-selective sulfonylation and modular edition of monosaccharides for hydroxyl group stereoinversion and swapping.Nature communications · 2026Article
- Iron-catalyzed stereoselective glycosylation for 1,2-cis-aminoglycoside assembly.Nature protocols · 2026Review
- Catalyst-Controlled Chemoselective β-Mannosylation of Phenols Via Attractive Noncovalent Interactions.Journal of the American Chemical Society · 2026Article
- Confined Acids Catalyze a Broadly Applicable β-SelectiveJournal of the American Chemical Society · 2026Article
- Hypervalent chalcogenonium organocatalysis for the direct stereoselective synthesis of deoxyglycosides from hemiacetals.Chemical science · 2026Article
- Stereospecific Synthesis of 2-Deoxy-2-fluoroglycosides via SCCS chemistry · 2026Article
- Hexafluoroisopropanol-Promoted Stereospecific Glycosylation Enables Efficient Access to N-O-Linked 1,2-JACS Au · 2025Article
- Development, Scope, and Catalyst Selection in Boron-Catalyzed Iterative Glycosylation.Journal of the American Chemical Society · 2025Article
- Progress on the synthesis and applications of the green non-ionic surfactant alkyl polyglycosides.RSC advances · 2025Review
- Article
- Mechanism of 3-The Journal of organic chemistry · 2025Article
- (Salen)Metal-Catalyzed β-Glucuronidation of Alcohols, Phenols, and Anilines.Journal of the American Chemical Society · 2025Article
- Catalytic Strategies for Stereoselective Carbohydrate Synthesis: Emerging Concepts for Accessing Challenging Glycosides.Angewandte Chemie (International ed. in English) · 2025Review
- The impact of supramolecular self-association of organocatalysts on catalytic performance.Nature reviews. Chemistry · 2025Review
- Iron-Catalyzed Stereoselective Nitrogen Atom Transfer for 1,2-Synlett : accounts and rapid communications in synthetic organic chemistry · 2025Article
- A broadly applicable stereospecific glycosylation.Nature synthesis · 2025Article
- Emerging Capabilities of Nonclassical Noncovalent Interactions and Asymmetric Catalysis in Stereoselective Glycosylations and Carbohydrate Functionalizations.Accounts of chemical research · 2025Article
- Article
52 more citing papers are in PubMed but not listed here.
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Authors and funding
6 authors at 1 institution in 1 country.
Funding
Abstract
Carbohydrates are involved in nearly all aspects of biochemistry, but their complex chemical structures present long-standing practical challenges to their synthesis. In particular, stereochemical outcomes in glycosylation reactions are highly dependent on the steric and electronic properties of coupling partners; thus, carbohydrate synthesis is not easily predictable. Here we report the discovery of a macrocyclic bis-thiourea derivative that catalyzes stereospecific invertive substitution pathways of glycosyl chlorides. The utility of the catalyst is demonstrated in the synthesis of trans-1,2-, cis-1,2-, and 2-deoxy-β-glycosides. Mechanistic studies are consistent with a cooperative mechanism in which an electrophile and a nucleophile are simultaneously activated to effect a stereospecific substitution reaction.
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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.