{"title":"Visible-Light-Mediated Synthesis of Anomeric <i>S</i>-Aryl Glycosides via Electron Donor-Acceptor Complex Using Thianthrenium Salts.","authors":"Zhuoyi Zhou, Yufeng Zhang, Zhiqiang Yu, Yuping Liu, Zhen Wang, Qingju Zhang, Liming Wang","doi":"10.3390/molecules30061315","DOIUrl":null,"url":null,"abstract":"<p><p><i>S</i>-Aryl glycosides are not only popular glycosyl donors in carbohydrate chemistry but also serve as valuable tools in various biological studies, which has brought significant attention to their preparation. However, there remains a pressing need for greener synthesis methods in this area. In response, a mild, sustainable, and metal- and photocatalyst-free electron donor-acceptor (EDA)-mediated approach for synthesizing <i>S</i>-Aryl glycosides using 1-thiosugar and aryl thianthrenium salt was developed. Our strategy utilizes 1-thiosugar as the donor, overcoming the traditional reliance on electron-rich thiols, such as aryl or carbonyl thiols, typically required for forming EDA complexes.</p>","PeriodicalId":19041,"journal":{"name":"Molecules","volume":"30 6","pages":""},"PeriodicalIF":4.2000,"publicationDate":"2025-03-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11946794/pdf/","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Molecules","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.3390/molecules30061315","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
引用次数: 0
Abstract
S-Aryl glycosides are not only popular glycosyl donors in carbohydrate chemistry but also serve as valuable tools in various biological studies, which has brought significant attention to their preparation. However, there remains a pressing need for greener synthesis methods in this area. In response, a mild, sustainable, and metal- and photocatalyst-free electron donor-acceptor (EDA)-mediated approach for synthesizing S-Aryl glycosides using 1-thiosugar and aryl thianthrenium salt was developed. Our strategy utilizes 1-thiosugar as the donor, overcoming the traditional reliance on electron-rich thiols, such as aryl or carbonyl thiols, typically required for forming EDA complexes.
期刊介绍:
Molecules (ISSN 1420-3049, CODEN: MOLEFW) is an open access journal of synthetic organic chemistry and natural product chemistry. All articles are peer-reviewed and published continously upon acceptance. Molecules is published by MDPI, Basel, Switzerland. Our aim is to encourage chemists to publish as much as possible their experimental detail, particularly synthetic procedures and characterization information. There is no restriction on the length of the experimental section. In addition, availability of compound samples is published and considered as important information. Authors are encouraged to register or deposit their chemical samples through the non-profit international organization Molecular Diversity Preservation International (MDPI). Molecules has been launched in 1996 to preserve and exploit molecular diversity of both, chemical information and chemical substances.