反应详情

To a solution of ethyl 1-[(1R,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[(4-ethoxy phenyl) methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]ethyl carbonate 12a (76.3 g, 0.09 mmol) in a methanol/tetrahydrofuran mixture (v/v=4/1, 10 mL) were added o-dichlorobenzene (0.05 mL, 0.48 mmol) and 10% Pd/C (12 mg, 0.01 mmol) at room temperature. The mixture was stirred at room temperature under H2 for 4 hours and filtered. The filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=1/4 to give the title compound 12 as a light yellow solid (38 mg, 60%, HPLC: 89.7%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 523.2 [M+H]+; and 1H NMR (400 MHz, DMSO-d6) δ(ppm): 7.40 (m, 2H), 7.29 (m, 1H), 7.09 (s, 2H), 6.83 (m, 2H), 5.59 (d, 1H), 5.13 (d, 1H), 5.02 (d, 1H), 4.93 (m, 1H), 4.14-4.02 (m, 3H), 4.02-3.92 (m, 4H), 3.55 (d, 2H), 3.47-3.37 (m, 2H), 1.31 (m, 6H), 1.19 (t, 3H).

1. filtrationfiltered
2. concentrationThe filtrate was concentrated in vacuo
3. customThe residue was purified by silica gel chromatography
4. washeluted with PE/EtOAc(v/v)=1/4