1,2-Dichlorobenzene → (1R,2S,3S,4R,5S)-5-[4-chloro-3-[[4-(trifluoromethoxy)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-[4-(trifluoromethoxy) phenyl]methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]ethanol 15q (102 mg, 0.13 mmol) in a methanol/tetrahydrofuran mixture (v/v=4/1, 10 mL) were added o-dichlorobenzene (95 mg, 0.65 mmol) and 10% Pd/C (41 mg, 0.39 mmol) at room temperature. The mixture was stirred under H2 at room temperature for 2 hours and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=1/5 to give the title compound 15 as a white solid (18 mg, 28.2%, HPLC: 96.2%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 535.2[M+HCOO]−; and 1H NMR (400 MHz, DMSO-d6) δ(ppm): 7.47 (d, 1H), 7.42 (d, 1H), 7.37-7.26 (m, 5H), 5.27 (d, 1H), 4.92 (m, 2H), 4.61 (d, 1H), 4.12 (s, 2H), 4.01 (dd, 1H), 3.81 (dd, 1H), 3.54 (d, 1H), 3.47-3.37 (m, 3H), 1.17 (d, 3H).

Provenance & Evidence