ArticleChemistry (Weinheim an der Bergstrasse, Germany)2020
Photoinitiated Thiol-ene Reactions of Enoses: A Powerful Tool for Stereoselective Synthesis of Glycomimetics with Challenging Glycosidic Linkages.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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9 citing papers in PubMed.
- Thioglycoside functionalizationChemical communications (Cambridge, England) · 2025Article
- Bispecific Thio-Linked Disaccharides as Inhibitors of Pseudomonas Aeruginosa Lectins LecA (PA-IL) and LecB (PA-IIL): Dual-Targeting Strategy.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Transformations of carbohydrate derivatives enabled by photocatalysis and visible light photochemistry.Chemical science · 2024Review
- In vitro and in vivo antiplasmodial evaluation of sugar-modified nucleoside analogues.Scientific reports · 2023Article
- Synthesis and Anticancer and Antiviral Activities of C-2'-Branched Arabinonucleosides.International journal of molecular sciences · 2022Article
- The Very First Modification of Pleuromutilin and Lefamulin by Photoinitiated Radical Addition Reactions-Synthesis and Antibacterial Studies.Pharmaceutics · 2021Article
- Transition-metal-free synthesis of aryl 1-thioglycosides with arynes at room temperature.RSC advances · 2021Article
- Synthesis and photoinitiated thiol-ene reactions ofRSC advances · 2020Article
- Photoinitiated Thiol-ene Reactions of Enoses: A Powerful Tool for Stereoselective Synthesis of Glycomimetics with Challenging Glycosidic Linkages.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
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Abstract
Thioglycosides and C-glycosides represent pharmacologically useful classes of glycomimetics that possess a high degree of biological stability. One emerging tool for the stereoselective synthesis of thioglycosides is the photoinitiated addition of thiols to unsaturated sugars. Moreover, thiyl radical-mediated reactions of exo-glycals and 1-substituted endo-glycals offer facile routes to β-C-glycosidic structures. This Concept article summarizes the thiol-ene coupling strategies developed recently by our group and Somsák's group for the synthesis of several kinds of glycomimetics which are difficult to synthesize by conventional methods. One unusual characteristic of the thiol-ene reactions of endo-glycals is that heating inhibits, whereas cooling promotes the reaction. This unique temperature dependence as well as the effects of the enose structures and thiol configurations on the efficacy and stereoselectivity of the reactions are also discussed.
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