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{"title":"Synthesis of 4′-Selenoribonucleosides, the Building Blocks of 4′-SelenoRNA, Using a Hypervalent Iodine","authors":"Noriko Saito-Tarashima, Masashi Ota, Noriaki Minakawa","doi":"10.1002/cpnc.34","DOIUrl":null,"url":null,"abstract":"<p>Herein is described a detailed protocol for the synthesis of 4′-selenoribonucleoside derivatives that involves the use of a hypervalent iodine species. These derivatives are versatile units for the preparation of 4′-selenoRNA. Large-scale synthesis of a 4-selenosugar starting from <span>D</span>-ribose is achieved in eight steps, including a final chromatographic purification. The resulting 4-selenosugar is then subjected to the one-pot Pummerer-like reaction using hypervalent iodine in the presence of silylated nucleobases. The reaction with silylated uracil affords the desired 4′-selenouridine derivatives with excellent β-selectivity and in good yield. Conversely, when purine nucleobases are used in the Pummerer-like reaction, N7 4′-selenoribonucleoside isomers are obtained alongside the desired N9 isomers. However, the undesired N7 isomers can be converted to the desired N9 ones under acidic conditions. © 2017 by John Wiley & Sons, Inc.</p>","PeriodicalId":10966,"journal":{"name":"Current Protocols in Nucleic Acid Chemistry","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2018-02-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/cpnc.34","citationCount":"4","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Current Protocols in Nucleic Acid Chemistry","FirstCategoryId":"1085","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/cpnc.34","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
Herein is described a detailed protocol for the synthesis of 4′-selenoribonucleoside derivatives that involves the use of a hypervalent iodine species. These derivatives are versatile units for the preparation of 4′-selenoRNA. Large-scale synthesis of a 4-selenosugar starting from D -ribose is achieved in eight steps, including a final chromatographic purification. The resulting 4-selenosugar is then subjected to the one-pot Pummerer-like reaction using hypervalent iodine in the presence of silylated nucleobases. The reaction with silylated uracil affords the desired 4′-selenouridine derivatives with excellent β-selectivity and in good yield. Conversely, when purine nucleobases are used in the Pummerer-like reaction, N7 4′-selenoribonucleoside isomers are obtained alongside the desired N9 isomers. However, the undesired N7 isomers can be converted to the desired N9 ones under acidic conditions. © 2017 by John Wiley & Sons, Inc.
利用高价碘合成4′-硒核苷,作为4′-硒核苷的组成部分
本文描述了合成4 ' -硒核糖核苷衍生物的详细方案,其中涉及使用高价碘种。这些衍生物是制备4′-selenoRNA的通用单元。从d -核糖开始大规模合成4-硒糖需要八个步骤,包括最后的色谱纯化。得到的4-硒糖然后在硅基化核碱基存在的情况下,使用高价碘进行一锅类似于彭默尔的反应。与硅基化尿嘧啶反应得到β选择性好、产率高的4′-硒尿嘧啶衍生物。相反,当嘌呤核碱基用于类pummer反应时,n74 ' -硒核糖核苷异构体与所需的N9异构体一起得到。然而,不需要的N7异构体可以在酸性条件下转化为所需的N9异构体。©2017 by John Wiley &儿子,Inc。
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