Ethyl Acetate → [(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(2,3-difluoro-4-methoxy-phenyl)methyl]phenyl]-6-methoxy-tetrahydropyran-2-yl]methanol

Participants

Reaction Steps

To a solution of tert-butyl-dimethyl-[[(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(2,3-difluoro-4-methoxy-phenyl)methyl]phenyl]-6-methoxy-tetrahydropyran-2-yl]methoxy]silane 21j (72.7 g, 86 mmol) in tetrahydrofuran (300 mL) was added tetrabutylammonium fluoride (172 mL, 172 mmol, 1 M in tetrahydrofuran) at room temperature. The mixture was stirred at room temperature for 12 hours, and then ethyl acetate was added (300 mL). The resulting mixture was washed with water (400 mL×4), 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)=20/1 to give the title compound 21k as yellow oil (21.0 g, 33.4%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, CDCl3) δ(ppm): 7.42-7.29 (m, 13H), 7.27-7.17 (m, 3H), 7.01 (m, 2H), 6.74-6.66 (m, 1H), 6.63-6.53 (m, 1H), 4.99-4.88 (m, 3H), 4.72 (m, 1H), 4.54 (d, 1H), 4.15-4.09 (m, 2H), 3.99-3.89 (m, 3H), 3.87 (s, 3H), 3.83 (d, 1H), 3.78-3.66 (m, 2H), 3.34 (d, 1H), 3.10 (s, 3H).

Provenance & Evidence