Regio- and Stereoselective Synthesis of 1-/3-Sulfone Sugars Controlled by the Amount of SnCl 4
Abstract
A SnCl 4 -mediated regioselective sulfonylation of glycal donors with sulfinic acids enables stereodivergent synthesis of 1-sulfone sugars (0–10 mol % SnCl 4 ) or 3-sulfone sugars (1 equiv of SnCl 4 ), respectively. Mechanistic studies reveal that sulfinic acid can activate the C3 leaving group alone to form sulfone glycosides, while excess SnCl 4 promotes the 1,3-shift to afford 3-sulfone sugars. The protocol exhibits broad substrate scope, including late-stage modification of natural products, with excellent regio-/stereoselectivity.
Fields of Study & Subjects
Carbohydrate Chemistry and Synthesis
Sulfur-Based Synthesis Techniques
Synthetic Organic Chemistry Methods
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 4
- Pages
- 1430–1435
- Publication date
- 21 January 2026
- Language
- EN