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{"title":"Stereoselective Synthesis of 4′-Selenonucleosides via the Seleno-Michael Reaction","authors":"Pramod K. Sahu, Dnyandev B. Jarhad, Gyudong Kim, Lak Shin Jeong","doi":"10.1002/cpnc.27","DOIUrl":null,"url":null,"abstract":"<p>5′-Homo-4′-selenonucleosides, a class of next-generation nucleosides, are synthesized from <span>D</span>-ribose via a 4-selenosugar intermediate. The key step in synthesizing this intermediate is a seleno-Michael reaction. 5′-Homo-4′-selenouridine and -adenosine are prepared using Pummerer-type and Vorbrüggen condensation, respectively. © 2017 by John Wiley & Sons, Inc.</p>","PeriodicalId":10966,"journal":{"name":"Current Protocols in Nucleic Acid Chemistry","volume":"69 1","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2017-06-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/cpnc.27","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Current Protocols in Nucleic Acid Chemistry","FirstCategoryId":"1085","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/cpnc.27","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"Chemistry","Score":null,"Total":0}
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Abstract
5′-Homo-4′-selenonucleosides, a class of next-generation nucleosides, are synthesized from D -ribose via a 4-selenosugar intermediate. The key step in synthesizing this intermediate is a seleno-Michael reaction. 5′-Homo-4′-selenouridine and -adenosine are prepared using Pummerer-type and Vorbrüggen condensation, respectively. © 2017 by John Wiley & Sons, Inc.
硒-迈克尔反应立体选择性合成4′-硒核苷
5′-同源-4′-硒核苷是由d -核糖经4-硒糖中间体合成的新一代核苷。合成该中间体的关键步骤是硒-迈克尔反应。采用pummerer缩合法和vorbrggen缩合法分别制备了5′-Homo-4′-硒脲和-腺苷。©2017 by John Wiley &儿子,Inc。
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