Tetrabutylammonium Fluoride → [(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[3-[(4-benzyloxyphenyl)methyl]-4-chloro-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-[3-[(4-benzyloxyphenyl)methyl]-4-chloro-phenyl]-6-methoxy-tetrahydropyran-2-yl]methoxy]silane 25g (2.26 g, 2.56 mmol) in anhydrous tetrahydrofuran (20 mL) was added tetrabutylammonium fluoride (5.12 mL, 5.12 mmol, 1 M in tetrahydrofuran) at room temperature. The mixture was stirred at room temperature for 12 hours, then quenched with water (60 mL) and partitioned. The aqueous layer was extracted with ethyl acetate (100 mL×2). The combined organic layers were washed with water (100 mL×2) and saturated aqueous sodium chloride (100 mL×2) in turn, 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 25h as a light yellow solid (0.54 g, 27.4%). The compound was characterized by the following spectroscopic data: 1H NMR (600 MHz, DMSO-d6) δ (ppm): 7.46 (m, 2H), 7.42 (m, 2H), 7.35-7.24 (m, 17H), 7.01 (m, 4H), 6.84 (m, 2H), 5.02 (s, 2H), 4.82-4.75 (m, 3H), 4.69 (d, 1H), 4.41 (d, 1H), 4.04 (m, 1H), 3.97 (t, 1H), 3.88 (d, 1H), 3.77 (d, 1H), 3.70 (m, 3H), 3.53 (m, 1H), 3.23 (d, 1H), 2.97 (s, 3H).

Provenance & Evidence