{"title":"Tetrafluoropyridin-4-yl thioglycosides (TFPTGs): Versatile donors in C-, O-, and N-glycosidic construction","authors":"Hong Cao , Hui Liu , Jin-Xi Liao , Jian-Song Sun","doi":"10.1016/j.tetlet.2025.155563","DOIUrl":null,"url":null,"abstract":"<div><div>Abstract</div><div>With glycosyl tetrafluoropyridin-4-yl thioglycosides (TFPTGs) as radical glycosylation donors, protocols to furnishing <em>C</em>-, <em>O</em>-, and <em>N</em>-glycosides have been established. TFPTGs represent the first type of donors amenable to forge both <em>C</em>- and <em>O</em>-/<em>N</em>-glycosidic linkages under light irradiation through radical glycosylation. For <em>C</em>- and <em>O</em>-glycosides, α-stereoselectivity was secured due to the stereoelectronic effect, while <em>N</em>-glycosides were obtained β-stereoselectively presumably because of <em>in situ</em> epimerization.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"160 ","pages":"Article 155563"},"PeriodicalIF":1.5000,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040403925001121","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
With glycosyl tetrafluoropyridin-4-yl thioglycosides (TFPTGs) as radical glycosylation donors, protocols to furnishing C-, O-, and N-glycosides have been established. TFPTGs represent the first type of donors amenable to forge both C- and O-/N-glycosidic linkages under light irradiation through radical glycosylation. For C- and O-glycosides, α-stereoselectivity was secured due to the stereoelectronic effect, while N-glycosides were obtained β-stereoselectively presumably because of in situ epimerization.
摘要以糖基四氟吡啶-4-基硫代糖苷（TFPTGs）作为自由基糖基化供体，建立了C-、O-和n-糖苷的供体方案。tfptg是第一种可以在光照射下通过自由基糖基化形成C-和O-/ n -糖苷键的供体。对于C-和o -糖苷，由于立体电子效应，获得了α-立体选择性，而n -糖苷可能是由于原位外映而获得β-立体选择性。
期刊介绍：
Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.
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
