Trifluoroacetic acid → HCID 86685135, compound

Participants

Reaction Steps

[(3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-yl]methanol 5k (1.2 g, 1.63 mmol) was dissolved in 25 mL dichloromethane, followed by dropwise addition of trifluoroacetic acid (0.5 mL, 6.52 mmol). The reaction mixture was stirred for 1.5 hours. Thereafter, the reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel chromatography with elution system D to obtain the title compound [(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]methanol 5m (580 mg, white solid), yield: 50.4%. MS m/z (ESI): 722.3 [M+18]; 1H NMR (400 MHz, CD3OD): δ 7.48-7.39 (m, 3H), 7.35-7.23 (m, 10H), 7.21-7.11 (m, 3H), 6.97 (s, 1H), 6.90 (d, 1H), 6.84 (d, 2H), 6.57 (d, 1H), 4.83 (d, 4H), 4.44 (t, 2H), 4.23 (m, 2H), 4.07-4.00 (m, 3H), 3.95 (dd, 1H), 3.87 (d, 1H), 3.79 (d, 1H), 3.73-3.69 (m, 2H), 3.56 (d, 1H), 3.01 (t, 2H).

Provenance & Evidence