Stereoselective Assembly of 2-Deoxy-2-fluoroglycosides Enabled by Pyridinium Catalysis
Abstract
2-Deoxy-2-fluoroglycosides are versatile chemical entities in glycoscience, functioning as enzyme probes, inhibitors, and valuable building blocks for bioactive glycomimetics. However, their efficient and stereoselective synthesis remains challenging. Herein, we report a pyridinium-salt-catalyzed highly stereoselective addition of an O-type glycosyl acceptor to 2-fluoroglycals, providing efficient access to a structurally diverse library of 2-fluoroglycosides. The excellent stereoselectivity favoring syn -addition and deuterated experimental results suggest a concerted mechanism. NMR titrations combined with DFT calculations demonstrate the presence of product inhibition and shed light on the reduced efficiency observed in the reactions involving electron-deficient phenols as well as alcoholic substrates.
Fields of Study & Subjects
Carbohydrate Chemistry and Synthesis
Fluorine in Organic Chemistry
Glycosylation and Glycoproteins Research
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 3
- Pages
- 995–1001
- Publication date
- 8 January 2026
- Language
- EN