Trimethylsilyl Chloride-Mediated Synthesis of 2-Deoxy Sugars: A Route to Substituted Chiral Quinoline-Based Glycohybrids
Abstract
Herein, we report a mild and effective trimethylsilyl chloride (TMSCl)-mediated method for the synthesis of diverse 2-deoxy sugars in excellent yields of up to 98% within 1 h from diverse protected glycals. Furthermore, we utilized these 2-deoxy sugars to synthesize stereochemically pure and diverse 2,4-substituted quinoline-based glycohybrids through a Cu(II)-catalyzed, multicomponent, one-pot cycloaddition reaction forming one new C-N bond and two C-C bonds. These 2,4-substituted chirally pure quinoline-based glycohybrids may have promising applications in medicinal chemistry. This versatile method enables the efficient synthesis of various 2-deoxy sugars and quinolines with inherent stereodiversity, easily scalable to gram scale quantities for broader applications.
Fields of Study & Subjects
Carbohydrate Chemistry and Synthesis
Click Chemistry and Applications
Cyclopropane Reaction Mechanisms
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 5
- Pages
- 1928–1937
- Publication date
- 21 January 2026
- Language
- EN