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

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Reaction Steps

[(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[[4-(2,2-difluoroethoxy)phenyl]methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]methanol 12m (76 mg, 0.10 mmol) was dissolved in 10 mL of mixed solution (THF and MeOH, v:v=1:1), followed by addition of o-dichlorobenzene (103 μL, 0.9 mmol) and Palladium/carbon (180 mg, 10%). The mixture was exchanged with H2 three times and stirred for 2 hours, then filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by column chromatography to obtain the title compound (1S,2S,3S,4R,5S)-5-[4-chloro-3-[[4-(2,2-difluoroethoxy)phenyl]methyl]phenyl]-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol 12 (17 mg, pale yellow solid), yield: 34.0%. MS m/z (ESI): 490.24 [M+18]; 1H NMR (400 MHz, CD3OD): δ 7.48-7.49 (m, 1H), 7.37-7.39 (m, 2H), 7.15-7.17 (d, 2H), 6.88-6.91 (d, 2H), 6.02-6.29 (ddt, 1H), 4.23-4.24 (d, 1H), 4.20-4.21 (d, 1H), 4.16-4.17 (d, 1H), 4.08 (s, 2H), 3.78-3.88 (m, 2H), 3.67-3.72 (m, 2H), 3.55-3.57 (m, 2H).

Provenance & Evidence