Stereoselective Thioconjugation by Photoinduced Thiol-ene Coupling Reactions of Hexo-and Pentopyranosyl d-and l-Glycals at Low-Temperature-Reactivity and Stereoselectivity Study

Viktor Kelemen; Mikljs Bege; Dániel Eszenyi; Njra Debreczeni; Attila Bényei; Tobias Sterzer; Pál Herczegh; Anikj Borbás

首页> 外文期刊>Chemistry: A European journal >Stereoselective Thioconjugation by Photoinduced Thiol-ene Coupling Reactions of Hexo-and Pentopyranosyl d-and l-Glycals at Low-Temperature-Reactivity and Stereoselectivity Study

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Stereoselective Thioconjugation by Photoinduced Thiol-ene Coupling Reactions of Hexo-and Pentopyranosyl d-and l-Glycals at Low-Temperature-Reactivity and Stereoselectivity Study

机译：通过光致硫代喹啉偶联反应在低温 - 反应性和立体选择性研究中对己唑和五羟吡喃糖基D-和L-族的偶联反应的立体选择性硫代谐波。

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摘要

A comprehensive optimization and mechanistic study on the photoinduced hydrothiolation of different dand 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-a-stereoselectivity in all cases. Hydrothiolation of 2-substituted pentoglycals resulted in mixtures of 1,2-cis-a-and -b-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.

机译：在RT至-120℃的温度范围内进行对不同阳乳糖和戊糖浆的综合优化和机械研究。在所有情况下，将硫醇加入到2取代的六重组上进行完整的1,2-CIS-A-立体选择性。取决于反应物的构型，2取代的戊糖浆的三烯化导致混合比的1,2-CIS-A-和-B-硫苷的混合物。未取代的族种在-80℃下的加致氢致胶质在绝佳的产率下进行，除了半乳球，提供具有高选择性的轴向C2-S连接的异构体。冷却总是有益于疗效，增加产量，并且在大多数情况下显着提高了立体选择性。建议的机制解释了中间碳中心基团的不同构象偏好，这是反应的立体选择性的关键因素。

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来源
《Chemistry: A European journal》 |2019年第64期|共17页
作者
Viktor Kelemen; Mikljs Bege; Dániel Eszenyi; Njra Debreczeni; Attila Bényei; Tobias Sterzer; Pál Herczegh; Anikj Borbás;
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作者单位

Department of Pharmaceutical Chemistry University of Debrecen Egyetem tér 1 4032 Debrecen (Hungary);

Department of Pharmaceutical Chemistry University of Debrecen Egyetem tér 1 4032 Debrecen (Hungary);

Department of Pharmaceutical Chemistry University of Debrecen Egyetem tér 1 4032 Debrecen (Hungary);

Department of Pharmaceutical Chemistry University of Debrecen Egyetem tér 1 4032 Debrecen (Hungary);

Department of Physical Chemistry University of Debrecen Egyetem tér 1 4032 Debrecen (Hungary);

Bruker AXS GmbH :stliche Rheinbreckenstra?e 49 76187 Karlsruhe (Germany);

Department of Pharmaceutical Chemistry University of Debrecen Egyetem tér 1 4032 Debrecen (Hungary);

Department of Pharmaceutical Chemistry University of Debrecen Egyetem tér 1 4032 Debrecen (Hungary);

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原文格式 PDF
正文语种 eng
中图分类应用化学;
关键词
glycal; photoactivation; stereoselective synthesis; thioglycoside; thiyl radical addition;

机译：Glycal;PhotoCtivation;立体选择合成;硫代糖苷;硫酸根加成;

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1. Stereoselective Thioconjugation by Photoinduced Thiol-ene Coupling Reactions of Hexo-and Pentopyranosyl d-and l-Glycals at Low-Temperature-Reactivity and Stereoselectivity Study [J] . Viktor Kelemen, Mikljs Bege, Dániel Eszenyi, Chemistry: A European journal . 2019,第64期

机译：通过光致硫代喹啉偶联反应在低温 - 反应性和立体选择性研究中对己唑和五羟吡喃糖基D-和L-族的偶联反应的立体选择性硫代谐波。
2. Science of Synthesis, Stereoselective Synthesis 3: Stereoselective Perkyclic Reactions, Cross Coupling, C-H and C-X Activation; edited by P. Andrew Evans, Georg Thieme Verlag: Stuttgart, 2011, hardcover, 1166 pp., european dollow2590, ISBN: 978-3-13-154131-4; softcover, 1066 pp., european dollow249, ISBN: 978-3-13-165181-5 [J] . Shuli You Synthesis: International Journal of Methods in Synthetic Organic Chemistry . 2011,第23期

机译：合成科学，立体选择合成3：立体选择性的性质反应，交叉偶联，C-H和C-X活化; 由P. Andrew Evans编辑，Georg Thieme Verlag：斯图加特，2011，精装，1166 PP，欧洲杜空间，ISBN：978-3-13-154131-4; Softcover，1066 pp，欧洲杜湿249，ISBN：978-3-13-165181-5
3. Science of Synthesis, Stereoselective Synthesis 3: Stereoselective Perkyclic Reactions, Cross Coupling, C-H and C-X Activation; edited by P. Andrew Evans, Georg Thieme Verlag: Stuttgart, 2011, hardcover, 1166 pp., european dollow2590, ISBN: 978-3-13-154131-4; softcover, 1066 pp., european dollow249, ISBN: 978-3-13-165181-5 [J] . Shuli You Synthesis: International Journal of Methods in Synthetic Organic Chemistry . 2011,第23期

机译：合成科学，立体选择合成3：立体选择性的性质反应，交叉偶联，C-H和C-X活化; 由P. Andrew Evans编辑，Georg Thieme Verlag：斯图加特，2011，精装，1166 PP，欧洲杜空间，ISBN：978-3-13-154131-4; Softcover，1066 pp，欧洲杜湿249，ISBN：978-3-13-165181-5
4. Regio-and Stereoselective Synthesis of Urushiols by Iron-CatalyzedCross-Coupling Reactions [C] . Ryosuke Agata, Hiroshi Matsuda, Siming Lu 日本化学会春季年会 . 2020

机译：铁催化剂联偶联反应的Regio-and立体选择合成尿道
5. Analysis of the factors that govern stereoselectivity in the reactions of oxocarbenium ion intermediates: The role of neighboring-group participation and the correlation between nucleophile strength and stereoselectivity. [D] . Beaver, Matthew Grant. 2010

机译：氧碳鎓离子中间体反应中控制立体选择性的因素分析：邻基参与的作用以及亲核试剂强度与立体选择性之间的关系。
6. Stereoselective Synthesis of Carbon-Sulfur-Bridged Glycomimetics by Photoinitiated Thiol-Ene Coupling Reactions [O] . Magdolna Csávás, Dániel Eszenyi, Erika Mező, 2020

机译：通过光引发的硫醇-烯偶联反应立体选择性地合成碳-硫桥接的糖代谢物
7. Stereoselective Thioconjugation by Photoinduced Thiol‐ene Coupling Reactions of Hexo‐ and Pentopyranosyl d ‐ and l ‐Glycals at Low‐Temperature—Reactivity and Stereoselectivity Study [O] . Viktor Kelemen, Miklós Bege, Dániel Eszenyi, 2019

机译：通过光致硫代喹啉-TI-烯酮偶联反应的立体选择性硫代喹啉，并在低温 - 反应性和立体选择性研究中偶联反应和L-Glycals

Stereoselective Thioconjugation by Photoinduced Thiol-ene Coupling Reactions of Hexo-and Pentopyranosyl d-and l-Glycals at Low-Temperature-Reactivity and Stereoselectivity Study

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