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

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Reaction Conditions

Reaction Steps

To a solution of tert-butyl-dimethyl-[[(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[4-(trifluoromethoxy)phenyl]methyl]phenyl]-6-methoxy-tetrahydropyran-2-yl]methoxy]silane 15j (5.27 g, 6.43 mmol) in tetrahydrofuran (35 mL) was added tetrabutylammonium fluoride (9.64 mL, 9.64 mmol, 1 M in tetrahydrofuran) at room temperature. The mixture was stirred at 45° C. for 48 hours. The reaction mixture was quenched with water (10 mL) and partitioned. The aqueous layer was extracted with ethyl acetate (20 mL×2). The combined organic layers were washed with saturated aqueous sodium chloride (20 mL×2), 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)=8/1 to give the title compound 15k as yellow oil (1.70 g, 35.3%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, CDCl3) δ (ppm): 7.45-7.30 (m, 13H), 7.26-7.17 (m, 3H), 7.14 (d, 2H), 7.08 (d, 2H), 7.01 (d, 2H), 4.99-4.87 (m, 3H), 4.71 (d, 1H), 4.56 (d 1H), 4.25-4.11 (m, 2H), 3.95 (m, 3H), 3.75 (m, 3H), 3.33 (d, 1H), 3.09 (s, 3H).

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