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

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Reaction Steps

To a solution of tert-butyl-dimethyl-[[(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[4-(2,2,2-trifluoroethoxyl)phenyl]methyl]phenyl]-6-methoxy-tetrahydropyran-2-yl]methoxy]silane 17g (23.7 g, 27.01 mmol) in tetrahydrofuran (100 mL) was added tetrabutylammonium fluoride (54.0 mL, 54.02 mmol, 1 M in tetrahydrofuran) at room temperature. The mixture was stirred at room temperature for 1 hour and then 40° C. for 12 hours. The reaction mixture was cooled to room temperature, and then 50 mL of saturated aqueous sodium bicarbonate and 100 mL of water were added. The resulting mixture was partitioned. The aqueous layer was extracted with ethyl acetate (80 mL×3). The combined organic layers were 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)=10/1 to give the title compound 17h as orange-yellow oil (5.5 g, 27.0%, HPLC: 84.7%). The compound was characterized by the following spectroscopic data: 1H NMR (600 MHz, CDCl3) δ (ppm): 7.39-7.30 (m, 12H), 7.21 (m, 4H), 7.07 (d, 2H), 7.00 (d, 2H), 6.80 (d, 2H), 4.98-4.86 (m, 3H), 4.70 (d, 1H), 4.50 (d, 1H), 4.34-4.24 (m, 2H), 4.11 (m, 2H), 3.95-3.86 (m, 3H), 3.80 (m, 1H), 3.73 (m, 1H), 3.70 (s, 1H), 3.30 (d, 1H), 3.07 (s, 3H).

Provenance & Evidence