Visible-Light-Mediated Synthesis of Anomeric <i>S</i>-Aryl Glycosides via Electron Donor–Acceptor Complex Using Thianthrenium Salts
<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 th...
Saved in:
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2025-03-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/30/6/1315 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1850280330268770304 |
|---|---|
| author | Zhuoyi Zhou Yufeng Zhang Zhiqiang Yu Yuping Liu Zhen Wang Qingju Zhang Liming Wang |
| author_facet | Zhuoyi Zhou Yufeng Zhang Zhiqiang Yu Yuping Liu Zhen Wang Qingju Zhang Liming Wang |
| author_sort | Zhuoyi Zhou |
| collection | DOAJ |
| description | <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. |
| format | Article |
| id | doaj-art-4686d4fbd19846d19a5f2067e30ed352 |
| institution | OA Journals |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-4686d4fbd19846d19a5f2067e30ed3522025-08-20T01:48:48ZengMDPI AGMolecules1420-30492025-03-01306131510.3390/molecules30061315Visible-Light-Mediated Synthesis of Anomeric <i>S</i>-Aryl Glycosides via Electron Donor–Acceptor Complex Using Thianthrenium SaltsZhuoyi Zhou0Yufeng Zhang1Zhiqiang Yu2Yuping Liu3Zhen Wang4Qingju Zhang5Liming Wang6National Research Centre for Carbohydrate Synthesis, College of Chemistry and Materials, Jiangxi Normal University, 99 Ziyang Avenue, Nanchang 330022, ChinaNational Research Centre for Carbohydrate Synthesis, College of Chemistry and Materials, Jiangxi Normal University, 99 Ziyang Avenue, Nanchang 330022, ChinaNational Research Centre for Carbohydrate Synthesis, College of Chemistry and Materials, Jiangxi Normal University, 99 Ziyang Avenue, Nanchang 330022, ChinaNational Research Centre for Carbohydrate Synthesis, College of Chemistry and Materials, Jiangxi Normal University, 99 Ziyang Avenue, Nanchang 330022, ChinaNational Research Centre for Carbohydrate Synthesis, College of Chemistry and Materials, Jiangxi Normal University, 99 Ziyang Avenue, Nanchang 330022, ChinaNational Research Centre for Carbohydrate Synthesis, College of Chemistry and Materials, Jiangxi Normal University, 99 Ziyang Avenue, Nanchang 330022, ChinaNational Research Centre for Carbohydrate Synthesis, College of Chemistry and Materials, Jiangxi Normal University, 99 Ziyang Avenue, Nanchang 330022, China<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.https://www.mdpi.com/1420-3049/30/6/1315<i>S</i>-Aryl glycosidesglycosylationEDA complexesvisible lightthianthrenium salts |
| spellingShingle | Zhuoyi Zhou Yufeng Zhang Zhiqiang Yu Yuping Liu Zhen Wang Qingju Zhang Liming Wang Visible-Light-Mediated Synthesis of Anomeric <i>S</i>-Aryl Glycosides via Electron Donor–Acceptor Complex Using Thianthrenium Salts Molecules <i>S</i>-Aryl glycosides glycosylation EDA complexes visible light thianthrenium salts |
| title | Visible-Light-Mediated Synthesis of Anomeric <i>S</i>-Aryl Glycosides via Electron Donor–Acceptor Complex Using Thianthrenium Salts |
| title_full | Visible-Light-Mediated Synthesis of Anomeric <i>S</i>-Aryl Glycosides via Electron Donor–Acceptor Complex Using Thianthrenium Salts |
| title_fullStr | Visible-Light-Mediated Synthesis of Anomeric <i>S</i>-Aryl Glycosides via Electron Donor–Acceptor Complex Using Thianthrenium Salts |
| title_full_unstemmed | Visible-Light-Mediated Synthesis of Anomeric <i>S</i>-Aryl Glycosides via Electron Donor–Acceptor Complex Using Thianthrenium Salts |
| title_short | Visible-Light-Mediated Synthesis of Anomeric <i>S</i>-Aryl Glycosides via Electron Donor–Acceptor Complex Using Thianthrenium Salts |
| title_sort | visible light mediated synthesis of anomeric i s i aryl glycosides via electron donor acceptor complex using thianthrenium salts |
| topic | <i>S</i>-Aryl glycosides glycosylation EDA complexes visible light thianthrenium salts |
| url | https://www.mdpi.com/1420-3049/30/6/1315 |
| work_keys_str_mv | AT zhuoyizhou visiblelightmediatedsynthesisofanomericisiarylglycosidesviaelectrondonoracceptorcomplexusingthianthreniumsalts AT yufengzhang visiblelightmediatedsynthesisofanomericisiarylglycosidesviaelectrondonoracceptorcomplexusingthianthreniumsalts AT zhiqiangyu visiblelightmediatedsynthesisofanomericisiarylglycosidesviaelectrondonoracceptorcomplexusingthianthreniumsalts AT yupingliu visiblelightmediatedsynthesisofanomericisiarylglycosidesviaelectrondonoracceptorcomplexusingthianthreniumsalts AT zhenwang visiblelightmediatedsynthesisofanomericisiarylglycosidesviaelectrondonoracceptorcomplexusingthianthreniumsalts AT qingjuzhang visiblelightmediatedsynthesisofanomericisiarylglycosidesviaelectrondonoracceptorcomplexusingthianthreniumsalts AT limingwang visiblelightmediatedsynthesisofanomericisiarylglycosidesviaelectrondonoracceptorcomplexusingthianthreniumsalts |