Subhankar Panda, Moyosore O Orimoloye, Tej Narayan Poudel, Steven De Jonghe, Dirk Jochmans, Johan Neyts, Courtney C Aldrich
{"title":"Protecting Group Control of Hydroxyketone-Hemiketal Tautomeric Equilibrium Enables the Stereoselective Synthesis of a 1<i>'</i>-Azido <i>C</i>-Nucleoside.","authors":"Subhankar Panda, Moyosore O Orimoloye, Tej Narayan Poudel, Steven De Jonghe, Dirk Jochmans, Johan Neyts, Courtney C Aldrich","doi":"10.1021/acs.joc.4c01981","DOIUrl":null,"url":null,"abstract":"<p><p>The synthesis of 1<i>'</i>-azido <i>C</i>-nucleosides is described to expand the set of azide-functionalized nucleosides for bioorthogonal applications and as potential antiviral drugs. Lewis acid-promoted azidation of a nucleoside hemiketal resulted in the formation of a tetrazole through a Schmidt reaction manifold. Conformational control to prevent ring-chain tautomerism enabled efficient 1<i>'</i>-azidation with complete β-diastereoselectivity. The unique reactivity and further derivation of the 1<i>'</i>-azido <i>C</i>-nucleosides are also reported.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3000,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"The Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c01981","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
The synthesis of 1'-azido C-nucleosides is described to expand the set of azide-functionalized nucleosides for bioorthogonal applications and as potential antiviral drugs. Lewis acid-promoted azidation of a nucleoside hemiketal resulted in the formation of a tetrazole through a Schmidt reaction manifold. Conformational control to prevent ring-chain tautomerism enabled efficient 1'-azidation with complete β-diastereoselectivity. The unique reactivity and further derivation of the 1'-azido C-nucleosides are also reported.
本研究介绍了 1'-azido C 核苷的合成，以扩大叠氮功能化核苷的范围，使其可用于生物正交应用并成为潜在的抗病毒药物。路易斯酸促进核苷半金属的叠氮化，通过施密特反应歧管形成四氮唑。为防止环链同分异构而进行的构象控制实现了具有完全 β-非对映选择性的高效 1'- 叠氮化反应。报告还介绍了 1'-azido C 核苷的独特反应性和进一步衍生。
期刊介绍：
The Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
