Palladium-Catalyzed Synthesis of S -Glycosides Via Stereoretentive Cross-Coupling
Abstract
-glycosides via cross-coupling, introducing for the first time a sugar aryl thioether as an electrophilic coupling partner. Our strategy focuses on developing an easily accessible, odorless, and bench-stable S-linked tetrazole glycosyl donor via a one-pot synthesis from free sugar, which subsequently serves as a strong electrophilic coupling partner with boronic acid. The reactivity and versatility of this reaction are demonstrated in over 30 examples, including different monosaccharides and disaccharides. Furthermore, the synthetic utility was highlighted by the synthesis of thiosugar analogues of ipragliflozin and dapagliflozin.
Fields of Study & Subjects
Carbohydrate Chemistry and Synthesis
Click Chemistry and Applications
Sulfur-Based Synthesis Techniques
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 22
- Pages
- 6907–6912
- Publication date
- 25 May 2026
- Language
- EN