ArticleAngewandte Chemie (International ed. in English)2020
A General Approach to O-Sulfation by a Sulfur(VI) Fluoride Exchange Reaction.
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 18 papers.
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Who cites it
18 citing papers in PubMed.
- Counteranion-mediated dynamic kinetic asymmetric fluorination to access sulfur-stereogenic center.Nature communications · 2026Article
- Chemical Strategies for Controlling Sulfation in Biomacromolecules.ACS chemical biology · 2026Review
- Organocatalytic Enantioselective Addition of 3-Aryloxindoles to Ethenesulfonyl Fluoride.Organic letters · 2025Article
- Chemical approaches to the sulfation of small molecules: current progress and future directions.Essays in biochemistry · 2024Review
- Palladium-Catalyzed Esterification of Aryl Fluorosulfates with Aryl Formates.Molecules (Basel, Switzerland) · 2024Article
- Modular synthesis of functional libraries by accelerated SuFEx click chemistry.Chemical science · 2024Article
- Dimethyl sulfate and diisopropyl sulfate as practical and versatile O-sulfation reagents.Nature communications · 2024Article
- Fluorosulfate as a Latent Sulfate in Peptides and Proteins.Journal of the American Chemical Society · 2023Article
- The Certainty of a Few Good Reactions.Chem · 2023Article
- Article
- Ethene-1,1-disulfonyl Difluoride (EDSF) for SuFEx Click Chemistry: Synthesis of SuFExable 1,1-Bissulfonylfluoride Substituted Cyclobutene Hubs.Angewandte Chemie (International ed. in English) · 2023Article
- Advances in the construction of diverse SuFEx linkers.National science review · 2023Review
- Sulfur fluoride exchange.Nature reviews. Methods primers · 2023Article
- Sulfation of Phenolic Acids: Chemoenzymatic vs. Chemical Synthesis.International journal of molecular sciences · 2022Article
- Reactive chemistry for covalent probe and therapeutic development.Trends in pharmacological sciences · 2022Review
- On resin synthesis of sulfated oligosaccharides.Chemical science · 2022Article
- Accelerated SuFEx Click Chemistry For Modular Synthesis.Angewandte Chemie (International ed. in English) · 2022Article
- Chain-Growth Sulfur(VI) Fluoride Exchange Polycondensation: Molecular Weight Control and Synthesis of Degradable Polysulfates.ACS central science · 2021Article
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6 authors.
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Abstract
O-sulfation is an important chemical code widely existing in bioactive molecules, but the scalable and facile synthesis of complex bioactive molecules carrying O-sulfates remains challenging. Reported here is a general approach to O-sulfation by the sulfur(VI) fluoride exchange (SuFEx) reaction between aryl fluorosulfates and silylated hydroxy groups. Efficient sulfate diester formation was achieved through systematic optimization of the electronic properties of aryl fluorosulfates. The versatility of this O-sulfation strategy was demonstrated in the scalable syntheses of a variety of complex molecules carrying sulfate diesters at various positions, including monosaccharides, disaccharides, an amino acid, and a steroid. Selective hydrolytic and hydrogenolytic removal of the aryl masking groups from sulfate diesters yielded the corresponding O-sulfate products in excellent yields. This strategy provides a powerful tool for the synthesis of O-sulfate bioactive compounds.
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