Chunyu Liu , Fazhan Liang , Yu Chen , Xianhua Pan , Zheng Xia
{"title":"Study on the fluorination of 1, 2-O-isopropylidene D-pentofuranose with DAST and its scalable application","authors":"Chunyu Liu , Fazhan Liang , Yu Chen , Xianhua Pan , Zheng Xia","doi":"10.1016/j.jfluchem.2023.110205","DOIUrl":null,"url":null,"abstract":"<div><p>The research focuses on the inversion of configuration at C3 of 1,2-<em>O</em>-isopropylidene<strong>-</strong><span>d</span>-arabinofuranoside and <span>d</span>-ribofuranoside promoted by DAST. Both the initial configuration and the presence of C5 acyl group in <span>d</span>-furanosides are the key factors for this inversion due to the formation of cyclic oxonium ion intermediates. This inversion of configuration has been successfully applied to scalable synthesis of <span>d</span>-lyxose and 2′,5′-di-<em>O</em>-benzoyl-3′-fluoro-3′-deoxy-β-<span>d</span>-ribofuranosyl-7-halogen-7-deazapurine.</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"272 ","pages":"Article 110205"},"PeriodicalIF":1.7000,"publicationDate":"2023-10-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Fluorine Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0022113923001203","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, INORGANIC & NUCLEAR","Score":null,"Total":0}
引用次数: 0
Abstract
The research focuses on the inversion of configuration at C3 of 1,2-O-isopropylidene-d-arabinofuranoside and d-ribofuranoside promoted by DAST. Both the initial configuration and the presence of C5 acyl group in d-furanosides are the key factors for this inversion due to the formation of cyclic oxonium ion intermediates. This inversion of configuration has been successfully applied to scalable synthesis of d-lyxose and 2′,5′-di-O-benzoyl-3′-fluoro-3′-deoxy-β-d-ribofuranosyl-7-halogen-7-deazapurine.
期刊介绍：
The Journal of Fluorine Chemistry contains reviews, original papers and short communications. The journal covers all aspects of pure and applied research on the chemistry as well as on the applications of fluorine, and of compounds or materials where fluorine exercises significant effects. This can include all chemistry research areas (inorganic, organic, organometallic, macromolecular and physical chemistry) but also includes papers on biological/biochemical related aspects of Fluorine chemistry as well as medicinal, agrochemical and pharmacological research. The Journal of Fluorine Chemistry also publishes environmental and industrial papers dealing with aspects of Fluorine chemistry on energy and material sciences. Preparative and physico-chemical investigations as well as theoretical, structural and mechanistic aspects are covered. The Journal, however, does not accept work of purely routine nature.
For reviews and special issues on particular topics of fluorine chemistry or from selected symposia, please contact the Regional Editors for further details.
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
