Cesium carbonate → HCID 20812491, compound

Participants

Reaction Steps

To a round bottom flask containing a solution of (S)-3-(5-Chloro-2-methoxy-phenyl)-1-chloromethyl-3-fluoro-6-trifluoromethyl-1,3-dihydro-indol-2-one (S)-IV) (0.486 g, 1.2 mmol) in anhydrous acetonitrile (9 mL) was added 2,3,4,6-tetra-O-benzyl-D-glucopyranose (V; 0.648 g, 1.2 mmol) and cesium carbonate (0.390 g, 1.2 mmol). The reaction mixture was allowed to stir at room temperature overnight. The solvent was then removed, and the crude product was purified via flash chromatography (silica gel, 5:1 hexanes:ethyl acetate) to give a 1:1 mixture of α and β anomers of the title compound (0.768 g, 71%). 1H NMR (CDCl3, 400 MHz): δ 7.79 (dd, 2H, J=5.1 Hz, 1.8 Hz), 7.37-7.12 (m, 48H), 6.66 (m, 2H), 5.66 (d, 1H, J=11.0 Hz), 5.34 (m, 2H), 5.08 (d, 1H, J=3.7 Hz), 4.89-4.73 (m, 9H), 4.66-4.44 (m, 9H), 3.79 (m, 3H), 3.73-3.59 (m, 6H), 3.55-3.49 (m, 3H), 3.38 (d, 6H, J=4.1 Hz).

Provenance & Evidence