Dániel Eszenyi
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Stereoselective Synthesis of Carbon-Sulfur-Bridged Glycomimetics by Photoinitiated Thiol-Ene Coupling Reactions Open
Oligosaccharides and glycoconjugates are abundant in all living organisms, taking part in a multitude of biological processes. The application of natural O-glycosides in biological studies and drug development is limited by their sensitivi…
Synthesis and photoinitiated thiol–ene reactions of <i>exo</i>-mannals – a new route to <i>C</i>-β-<span>d</span>-mannosyl derivatives Open
A synthetic procedure was elaborated for O-peracylated exo-mannals. Thiol-ene additions to pyranoid and furanoid exo-mannals gave mannosylmethyl sulfide type adducts with exclusive regio- and β(d)-stereoselectivities including disaccharide…
Cover Feature: Stereoselective Thioconjugation by Photoinduced Thiol‐ene Coupling Reactions of Hexo‐ and Pentopyranosyl <span>d</span>‐ and <span>l</span>‐Glycals at Low‐Temperature—Reactivity and Stereoselectivity Study (Chem. Eur. J. 64/2019) Open
Radical-mediated hydrothiolation of enoses was studied as a stereoselective method for synthesizing challenging oligosaccharide structures. Three types of glycals were reacted with various thiols using UV irradiation at the temperature ran…
Stereoselective Thioconjugation by Photoinduced Thiol‐ene Coupling Reactions of Hexo‐ and Pentopyranosyl <span>d</span>‐ and <span>l</span>‐Glycals at Low‐Temperature—Reactivity and Stereoselectivity Study Open
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‐…
Promotion of a Reaction by Cooling: Stereoselective 1,2‐<i>cis</i>‐α‐Thioglycoconjugation by Thiol‐Ene Coupling at −80 °C Open
The photoinitiated thiol‐ene coupling reactions of 2‐substituted glycals were studied as a generally applicable strategy for stereoselective 1,2‐ cis ‐α‐thioconjugation. Although all glycals reacted with full α‐selectivity, the efficacy of…
A Modular Synthetic Approach to Isosteric Sulfonic Acid Analogues of the Anticoagulant Pentasaccharide Idraparinux Open
Heparin-based anticoagulants are drugs of choice in the therapy and prophylaxis of thromboembolic diseases. Idraparinux is a synthetic anticoagulant pentasaccharide based on the heparin antithrombin-binding domain. In the frame of our ongo…
Synthesis of <i>C</i>‐2‐ and <i>C</i>‐3‐Sulfonatomethyl <i>O</i>‐ and <i>S</i>‐Glycosides by Horner–Wadsworth–Emmons Olefination Open
The applicability of the Horner–Wadsworth–Emmons olefination to the introduction of the sulfonatomethyl moiety at the 2‐ and 3‐positions of orthogonally protected O ‐ and S ‐glycosides has been studied. The conformational preferences and r…
Synthesis of thiodisaccharides by photoinduced hydrothiolation of 2-acetoxy glycals Open
Here, we present the synthesis of α-D-galactopyranosyl and α-L-fucopyranosyl thiodisaccharides 5-8 by the photoinitiated thiol-ene reactions of 2-acetoxy-3,4,6-tri-O-acetyl-D-galactal 1 and 2-acetoxy-3,4-di-O-acetyl-L-fucal 2 with thiols 3…
CCDC 1483395: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
CCDC 1483396: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …