Trimethylsilyl Chloride-Mediated Synthesis of 2-Deoxy Sugars: A Route to Substituted Chiral Quinoline-Based Glycohybrids

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.