User-Friendly Thioglycoside Preactivation via Instant Sulfenyl Chloride Generation
Abstract
Thioglycoside preactivation enables one-pot oligosaccharide assembly but relies on unstable sulfenyl chloride activators. We report a user-friendly manifold that forms sulfenyl chlorides in seconds from common thiols and N -chlorosuccinimide, with succinimide precipitating and the clear supernatant serving as a drop-in activator solution. The protocol tolerates the substrate scope, accommodating special stereoselective glycosylation reactions and iterative one-pot sequences. A concise synthesis of a human milk tetrasaccharide demonstrates rapid one-pot access to a biologically relevant motif.
Fields of Study & Subjects
Carbohydrate Chemistry and Synthesis
Click Chemistry and Applications
Chemical Synthesis and Analysis
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 7
- Pages
- 2386–2391
- Publication date
- 9 February 2026
- Language
- EN