Chemoselective synthesis of polyfunctional aminophenyl 2-oxobut-3-enyl - and quinoline-methyl-C-glycopyranosides from nitrophenyl 2-oxobut-3-enyl C-glycopyranosides under ultrasonic vibrationф

Abstract

Chemoselective reduction of nitro group in polyfunctional nitrophenyl 2-oxobut-3-enyl C-glycopyranosides to the respective aminophenyl 2-oxobut-3-enyl glycopyranosides with SnCl2.2H2O under ultrasonic vibration in good yields was achieved successfully. Other potentially reducible groups such as carbonyl, ester, azide, tosyl, alkenic substituents were unaffected during reaction. The 2′-nitrophenyl-2-oxobut-3-enyl glycopyranosides as reduction substrates gave 2-quinoline¬methyl glycopyranosides via reduction followed by intramolecular cyclocondensation reactions. These β-C-glycopyranosides hold great promise in medicinal chemistry.