可见光促进Ir(III)催化1-溴糖立体选择性合成azauracil - c核苷。

IF 5 1区 化学 Q1 CHEMISTRY, ORGANIC
Ramanand Das,Norein Sakander,Sanchari Kundu,Debaraj Mukherjee,Taraknath Kundu
{"title":"可见光促进Ir(III)催化1-溴糖立体选择性合成azauracil - c核苷。","authors":"Ramanand Das,Norein Sakander,Sanchari Kundu,Debaraj Mukherjee,Taraknath Kundu","doi":"10.1021/acs.orglett.5c01474","DOIUrl":null,"url":null,"abstract":"A visible light-promoted, mild, and efficient Ir(III)-catalyzed synthesis of C-nucleosides is reported, utilizing 1-bromosugar as the glycosyl radical precursor and 6-azauracil as the nucleobase. The method exhibits high α-selectivity and excellent functional group tolerance. Spectroscopic evidence shows that the coupling reaction happens via initial reductive quenching of the Ir(III) catalyst under visible light. Density functional theory calculation reveals the reason for complete α-selectivity. Finally, biologically active 6-aza pseudouridine analogues were synthesized, making the process a valuable platform for C-nucleosides.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"79 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2025-05-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Visible Light-Promoted Ir(III)-Catalyzed Stereoselective Synthesis of Azauracil-C-Nucleosides from 1-Bromosugar.\",\"authors\":\"Ramanand Das,Norein Sakander,Sanchari Kundu,Debaraj Mukherjee,Taraknath Kundu\",\"doi\":\"10.1021/acs.orglett.5c01474\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"A visible light-promoted, mild, and efficient Ir(III)-catalyzed synthesis of C-nucleosides is reported, utilizing 1-bromosugar as the glycosyl radical precursor and 6-azauracil as the nucleobase. The method exhibits high α-selectivity and excellent functional group tolerance. Spectroscopic evidence shows that the coupling reaction happens via initial reductive quenching of the Ir(III) catalyst under visible light. Density functional theory calculation reveals the reason for complete α-selectivity. Finally, biologically active 6-aza pseudouridine analogues were synthesized, making the process a valuable platform for C-nucleosides.\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"79 1\",\"pages\":\"\"},\"PeriodicalIF\":5.0000,\"publicationDate\":\"2025-05-20\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.orglett.5c01474\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.5c01474","RegionNum":1,"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

摘要

本文报道了一种可见光促进、温和、高效的Ir(III)催化合成c -核苷的方法,该方法利用1-溴糖作为糖基自由基前体,6-杜鹃酸作为核碱基。该方法具有较高的α选择性和良好的官能团耐受性。光谱证据表明,偶联反应是通过Ir(III)催化剂在可见光下的初始还原猝灭发生的。密度泛函理论计算揭示了α-完全选择性的原因。最后,合成了具有生物活性的6-aza假尿嘧啶类似物,使该工艺成为c -核苷的有价值的平台。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Visible Light-Promoted Ir(III)-Catalyzed Stereoselective Synthesis of Azauracil-C-Nucleosides from 1-Bromosugar.
A visible light-promoted, mild, and efficient Ir(III)-catalyzed synthesis of C-nucleosides is reported, utilizing 1-bromosugar as the glycosyl radical precursor and 6-azauracil as the nucleobase. The method exhibits high α-selectivity and excellent functional group tolerance. Spectroscopic evidence shows that the coupling reaction happens via initial reductive quenching of the Ir(III) catalyst under visible light. Density functional theory calculation reveals the reason for complete α-selectivity. Finally, biologically active 6-aza pseudouridine analogues were synthesized, making the process a valuable platform for C-nucleosides.
求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
来源期刊
Organic Letters
Organic Letters 化学-有机化学
CiteScore
9.30
自引率
11.50%
发文量
1607
审稿时长
1.5 months
期刊介绍: Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:604180095
Book学术官方微信