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

Participants

Reaction Conditions

Reaction Steps

To a solution of (2R,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[4-(2,2,2-trifluoroethoxyl) phenyl]methyl]phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-carbaldehyde 17j (4.80 g, 6.04 mmol) in methanol (50 mL) was added sodium borohydride (326 mg, 8.62 mmol) at −5° C. The mixture was stirred for 30 min at −5° C. The reaction mixture was quenched with saturated aqueous ammonium chloride (15 mL) and concentrated in vacuo to remove most of the solvent. To the residue was added water (50 mL). The mixture was extracted with ethyl acetate (30 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 17k as light yellow oil (2.7 g, 56.3%, HPLC: 89.2%). This material was not further purified. The compound was characterized by the following spectroscopic data: 1H NMR (600 MHz, DMSO-d6) δ(ppm): 7.53 (d, 2H), 7.40 (d, 1H), 7.33 (d, 2H), 7.31-7.22 (m, 12H), 7.08-7.01 (m, 4H), 6.89 (d, 2H), 4.90 (s, 1H), 4.85-4.74 (m, 3H), 4.71-4.63 (m, 3H), 4.52 (d, 1H), 4.30 (s, 1H), 4.05 (m, 3H), 3.99-3.85 (m, 3H), 3.79 (m, 2H), 3.54 (d, 1H), 3.19 (d, 1H), 3.09 (s, 3H).

Provenance & Evidence