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{"title":"Preparation of Pyrimidine Alkenyl Acyclic Nucleoside Phosphonoamidates","authors":"Elisa Pileggi, Michaela Serpi, Fabrizio Pertusati","doi":"10.1002/cpnc.56","DOIUrl":null,"url":null,"abstract":"<p>This synthetic protocol describes two strategies for the preparation of pyrimidine alkenyl acyclic nucleoside phosphonoamidates (ANPs), including linear and trisubstituted alkenyl derivatives. For the first procedure, a bis-trimethylsilyl ester of the parent alkenyl ANPs is the key intermediate that reacts with the desired amino acid ester and aryl alcohol. For the second procedure, an allyl phosphonoamidate bearing the ProTide promoieties is the key synthon employed as olefin partner for a cross-metathesis reaction with an alkylated nucleobase. © 2018 by John Wiley & Sons, Inc.</p>","PeriodicalId":10966,"journal":{"name":"Current Protocols in Nucleic Acid Chemistry","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2018-08-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/cpnc.56","citationCount":"2","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Current Protocols in Nucleic Acid Chemistry","FirstCategoryId":"1085","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/cpnc.56","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 synthetic protocol describes two strategies for the preparation of pyrimidine alkenyl acyclic nucleoside phosphonoamidates (ANPs), including linear and trisubstituted alkenyl derivatives. For the first procedure, a bis-trimethylsilyl ester of the parent alkenyl ANPs is the key intermediate that reacts with the desired amino acid ester and aryl alcohol. For the second procedure, an allyl phosphonoamidate bearing the ProTide promoieties is the key synthon employed as olefin partner for a cross-metathesis reaction with an alkylated nucleobase. © 2018 by John Wiley & Sons, Inc.
嘧啶烯基无环核苷膦酸酯的制备
本合成方案描述了制备嘧啶烯基无环核苷膦酸酯(ANPs)的两种策略，包括线性和三取代烯基衍生物。在第一个过程中，母体烯基ANPs的双三甲基硅基酯是与所需氨基酸酯和芳基醇反应的关键中间体。在第二个过程中，带有ProTide促进基团的烯丙基磷酰胺是与烷基化核碱基交叉复分解反应的关键合成物，用作烯烃伙伴。©2018 by John Wiley &儿子,Inc。
本文章由计算机程序翻译，如有差异，请以英文原文为准。
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