Ethyl Acetate → HCID 86685120, compound

Participants

Reaction Steps

To a solution of tert-butyl-dimethyl-[[(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(4-ethoxy-2,3-difluoro-phenyl)methyl]phenyl]-6-methoxy-tetrahydropyran-2-yl]methoxy]silane 23i (16.29 g, 18.95 mmol) in tetrahydrofuran (100 mL) was added tetrabutylammonium fluoride (37.9 mL, 37.9 mmol, 1 M in tetrahydrofuran) at room temperature. The mixture was stirred at room temperature for 12 hours, and then ethyl acetate (200 mL) was added. The resulting mixture was washed with saturated aqueous sodium chloride (100 mL×3), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=15/1 to give the title compound 23j as a yellow solid (4.42 g, 31%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, CDCl3) δ(ppm): 7.29 (m, 10H), 7.22 (s, 2H), 7.5 (m, 4H), 6.95 (m, 2H), 6.76 (m, 1H), 6.51 (m, 1H), 4.92 (m, 3H), 4.66 (d, 1H), 4.47 (d, 1H), 4.14 (m, 1H), 4.03 (m, 3H), 3.88 (m, 3H), 3.77 (m, 1H), 3.66 (m, 2H), 3.27 (d, 1H), 3.05 (s, 3H), 1.39 (t, 3H).

Provenance & Evidence