(2R,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-carbaldehyde → HCID 118377802, compound

Participants

Reaction Steps

To a solution of (2R,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(4-ethoxyphenyl) methyl]phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-carbaldehyde 8a (1.38 g, 1.88 mmol) in tetrahydrofuran (30 mL) was added dropwise methylmagnesium bromide (1.9 mL, 5.63 mL) at room temperature. The mixture was stirred at room temperature for 45 min under N2 and quenched with 10 mL of saturated aqueous ammonium chloride. Most of the solvent of the mixture was removed in vacuo. The resulting mixture was extracted with ethyl acetate (10 mL×2). The combined organic layers were washed with saturated aqueous sodium chloride (5 mL×2), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=8/1 to give the title compound 8b as colourless oil (414 mg, 30.0%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, DMSO-d6) δ (ppm): 7.55 (m, 1H), 7.46 (d, 1H), 7.40 (d, 1H), 7.35-7.30 (m, 5H), 7.30-7.23 (m, 8H), 7.00 (m, 4H), 6.74 (d, 2H), 5.03 (t, 1H), 4.72 (m, 4H), 4.53 (d, 1H), 4.49 (d, 1H), 4.42 (d, 1H), 4.18 (m, 2H), 4.05 (d, 1H), 3.94 (m, 2H), 3.89 (d, 1H), 3.85-3.77 (m, 2H), 3.73 (m, 1H), 3.43 (d, 1H), 2.92 (s, 3H), 1.28 (t, 3H), 1.23 (d, 3H).

Provenance & Evidence