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

Participants

Reaction Steps

To a solution of 1-[(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3[(4-ethoxyphenyl)methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octane-1-yl]propan-1-ol 3a (42 mg, 0.06 mmol) in a methanol/tetrahydrofuran mixture (v/v=4/1, 5 mL) were added o-dichlorobenzene (41.16 mg, 0.28 mmol) and 10% Pd/C (5.72 mg, 0.006 mmol) in turn. The mixture was stirred at room temperature under H2 for 4 hours and filtered. The filtered cake was washed with a methanol/tetrahydrofuran mixture (v/v=4/1, 10 mL×2). The combined filtrates were concentrated in vacuo. The residue was purified to give the title compound 3 as a pale yellow solid (76.5 mg, 51.0%, HPLC: 94.6%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 465.1[M+H]+; and 1H NMR (400 MHz, CDCl3) δ(ppm): 7.35 (m, 2H), 7.32 (m, 1H), 7.06 (d, 2H), 6.77 (d, 2H), 4.19 (d, 1H), 4.10 (d, 1H), 3.96 (m, 4H), 3.76 (m, 3H), 3.68 (m, 1H), 1.54 (m, 2H), 1.36 (t, 3H), 0.95 (t, 3H).

Provenance & Evidence