1,2-Dichlorobenzene → (1R,2S,3S,4R,5S)-5-[4-chloro-3-[[4-(2,2,2-trifluoroethoxyl)phenyl]methyl]phenyl]-1-(1-hydroxyethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol

Participants

Reaction Steps

To a solution of 1-[(1R,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[[4-(2,2,2-trifluoroethoxyl) phenyl]methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]ethanol 17n (350.0 mg, 0.45 mmol) in a methanol/tetrahydrofuran mixture (v/v=4/1, 15 mL) were added o-dichlorobenzene (0.25 mL, 2.25 mmol) and 10% Pd/C (50.0 mg, 0.04 mmol) at room temperature. The mixture was stirred at room temperature under H2 for 3 hours and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=3/1 to give a few white solid. Then the solid was further purified by prep-HPLC to give the title compound 17 as a white solid (70.5 mg, 30.7%, HPLC: 90.5%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 505.20 [M+H]+; and 1H NMR (600 MHz, DMSO-d6) δ(ppm): 7.41 (m, 2H), 7.31 (d, 1H), 7.15 (d, 2H), 6.97 (d, 2H), 5.31 (m, 1H), 4.85 (m, 2H), 4.68 (m, 2H), 4.64 (d, 1H), 4.02 (m, 1H), 3.98 (d, 2H), 3.83 (q, 1H), 3.76 (d, 1H), 3.54 (m, 1H), 3.43 (m, 2H), 1.16 (d, 3H).

Provenance & Evidence