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{"title":"Nucleoside-O-Methyl-(H)-Phosphinates: Novel Monomers for the Synthesis of Methylphosphonate Oligonucleotides Using H-Phosphonate Chemistry","authors":"Ondřej Kostov, Ondřej Páv, Ivan Rosenberg","doi":"10.1002/cpnc.35","DOIUrl":null,"url":null,"abstract":"<p>This unit comprises the straightforward synthesis of protected 2′-deoxyribonucleoside-<i>O</i>-methyl-(H)-phosphinates in both 3′- and 5′-series. These compounds represent a new class of monomers compatible with the solid-phase synthesis of oligonucleotides using H-phosphonate chemistry and are suitable for the preparation of both 3′- and 5′-<i>O</i>-methylphosphonate oligonucleotides. The synthesis of 4-toluenesulfonyloxymethyl-(H)-phosphinic acid as a new reagent for the preparation of <i>O</i>-methyl-(H)-phosphinic acid derivatives is described. © 2017 by John Wiley & Sons, Inc.</p>","PeriodicalId":10966,"journal":{"name":"Current Protocols in Nucleic Acid Chemistry","volume":"70 1","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2018-02-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/cpnc.35","citationCount":"1","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Current Protocols in Nucleic Acid Chemistry","FirstCategoryId":"1085","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/cpnc.35","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
This unit comprises the straightforward synthesis of protected 2′-deoxyribonucleoside-O -methyl-(H)-phosphinates in both 3′- and 5′-series. These compounds represent a new class of monomers compatible with the solid-phase synthesis of oligonucleotides using H-phosphonate chemistry and are suitable for the preparation of both 3′- and 5′-O -methylphosphonate oligonucleotides. The synthesis of 4-toluenesulfonyloxymethyl-(H)-phosphinic acid as a new reagent for the preparation of O -methyl-(H)-phosphinic acid derivatives is described. © 2017 by John Wiley & Sons, Inc.
核苷- o -甲基-(H)-膦酸盐:用H-膦酸盐化学合成甲基膦酸寡核苷酸的新单体
该单元包括3 '和5 '系列的受保护的2 ' -脱氧核糖核苷- o -甲基-(H)-膦酸盐的直接合成。这些化合物代表了一类与h -膦酸盐固相合成寡核苷酸兼容的新单体,适用于制备3 ' -和5 ' - o -甲基膦酸寡核苷酸。介绍了4-甲苯磺酰氧基甲基-(H)-膦酸的合成,作为制备邻甲基-(H)-膦酸衍生物的新试剂。©2017 by John Wiley &儿子,Inc。
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