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

Participants

Reaction Steps

To a solution of (2R,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[4-(trifluoromethoxy) phenyl]methyl]phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-carbaldehyde 15m (1.26 g, 1.59 mmol) in anhydrous methanol (30 mL) was added sodium borohydride (120 mg, 23.18 mmol) in portions at 0° C. The mixture was warmed up to room temperature and stirred for 30 min. The reaction mixture was quenched with water (5 mL) and extracted with ethyl acetate (20 mL×2). The combined organic layers were washed with saturated aqueous sodium chloride (10 mL×2), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound 15n as yellow oil (570 mg, 46.0%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, CD3OD) δ(ppm): 7.58 (dd, 1H), 7.54 (d, 1H), 7.39 (d, 1H), 7.32 (m, 5H), 7.25 (m, 8H), 7.16 (d, 2H), 7.09 (m, 4H), 4.94 (d, 1H), 4.90 (d, 1H), 4.80 (s, 1H), 4.76 (d, 1H), 4.63 (t, 1H), 4.24 (t, 1H), 4.14 (dd, 2H), 4.07 (s, 3H), 4.00-3.93 (m, 2H), 3.77 (d, 1H), 3.37 (dd, 1H), 3.18 (s, 3H).

Provenance & Evidence