Sergey N. Mikhailov, Mikhail S. Drenichev, Vladimir E. Oslovsky, Irina V. Kulikova, Piet Herdewijn
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{"title":"含2′‐O‐α‐D‐核糖呋喃基腺苷的聚(ADP‐核糖)单体的合成","authors":"Sergey N. Mikhailov, Mikhail S. Drenichev, Vladimir E. Oslovsky, Irina V. Kulikova, Piet Herdewijn","doi":"10.1002/cpnc.92","DOIUrl":null,"url":null,"abstract":"<p>In this article, the earlier reported procedure for the synthesis of 2′-<i>O</i>-β-<span>D</span>-ribofuranosyl nucleosides was extended to the synthesis of 2′-<i>O</i>-α-<span>D</span>-ribofuranosyl adenosine, a monomeric unit of poly(ADP-ribose). It consists in condensation of a small excess of 1-<i>O</i>-acetyl-2,3,5-tri-<i>O</i>-benzoyl-α,β-<span>D</span>-arabinofuranose activated with tin tetrachloride with 3′,5′-<i>O</i>-tetra-isopropyldisiloxane-1,3-diyl-ribonucleosides in 1,2-dichloroethane. The following debenzoylation and silylation of arabinofuranosyl residue and inversion of configuration at C-2ʹʹ atom of arabinofuranosyl residue and final removal of silyl protective groups gave 2′-<i>O</i>-α-<span>D</span>-ribofuranosyl adenosine in overall 13% to 21% yield. © 2019 by John Wiley & Sons, Inc.</p>","PeriodicalId":10966,"journal":{"name":"Current Protocols in Nucleic Acid Chemistry","volume":"78 1","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2019-07-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/cpnc.92","citationCount":"1","resultStr":"{\"title\":\"Synthesis of Poly(ADP-ribose) Monomer Containing 2′-O-α-D-Ribofuranosyl Adenosine\",\"authors\":\"Sergey N. Mikhailov, Mikhail S. Drenichev, Vladimir E. Oslovsky, Irina V. Kulikova, Piet Herdewijn\",\"doi\":\"10.1002/cpnc.92\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>In this article, the earlier reported procedure for the synthesis of 2′-<i>O</i>-β-<span>D</span>-ribofuranosyl nucleosides was extended to the synthesis of 2′-<i>O</i>-α-<span>D</span>-ribofuranosyl adenosine, a monomeric unit of poly(ADP-ribose). It consists in condensation of a small excess of 1-<i>O</i>-acetyl-2,3,5-tri-<i>O</i>-benzoyl-α,β-<span>D</span>-arabinofuranose activated with tin tetrachloride with 3′,5′-<i>O</i>-tetra-isopropyldisiloxane-1,3-diyl-ribonucleosides in 1,2-dichloroethane. The following debenzoylation and silylation of arabinofuranosyl residue and inversion of configuration at C-2ʹʹ atom of arabinofuranosyl residue and final removal of silyl protective groups gave 2′-<i>O</i>-α-<span>D</span>-ribofuranosyl adenosine in overall 13% to 21% yield. © 2019 by John Wiley & Sons, Inc.</p>\",\"PeriodicalId\":10966,\"journal\":{\"name\":\"Current Protocols in Nucleic Acid Chemistry\",\"volume\":\"78 1\",\"pages\":\"\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2019-07-16\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://sci-hub-pdf.com/10.1002/cpnc.92\",\"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.92\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"Chemistry\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Current Protocols in Nucleic Acid Chemistry","FirstCategoryId":"1085","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/cpnc.92","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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