ArticleChemistry (Weinheim an der Bergstrasse, Germany)2019
Stereoselective Thioconjugation by Photoinduced Thiol-ene Coupling Reactions of Hexo- and Pentopyranosyl d- and l-Glycals at Low-Temperature-Reactivity and Stereoselectivity Study.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2019. 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.
- 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
- 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
- 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
- Photoinitiated Thiol-Ene Reactions of Various 2,3-Unsaturated O-, C- S- and N-Glycosides - Scope and Limitations Study.Chemistry, an Asian journal · 2020Article
- Stereoselective Synthesis of Carbon-Sulfur-Bridged Glycomimetics by Photoinitiated Thiol-Ene Coupling Reactions.International journal of molecular sciences · 2020Article
- Stereoselective Thioconjugation by Photoinduced Thiol-ene Coupling Reactions of Hexo- and Pentopyranosyl d- and l-Glycals at Low-Temperature-Reactivity and Stereoselectivity Study.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019Article
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8 authors.
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Abstract
A comprehensive optimization and mechanistic study on the photoinduced hydrothiolation of different d- and l- hexo- and pentoglycals with various thiols was performed, at the temperature range of RT to -120 °C. Addition of thiols onto 2-substituted hexoglycals proceeded with complete 1,2-cis-α-stereoselectivity in all cases. Hydrothiolation of 2-substituted pentoglycals resulted in mixtures of 1,2-cis-α- and -β-thioglycosides of varying ratio depending on the configuration of the reactants. Hydrothiolation of unsubstituted glycals at -80 °C proceeded with excellent yields and, except for galactal, provided the axially C2-S-linked isomers with high selectivity. Cooling was always beneficial to the efficacy, increased the yields and in most cases significantly raised the stereoselectivity. The suggested mechanism explains the different conformational preferences of the intermediate carbon-centered radicals, which is a crucial factor in the stereoselectivity of the reactions.
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