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.