Water → HCID 86685124, compound

Participants

Reaction Steps

To a solution of [(3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(4-ethoxy-2,3-difluoro-phenyl) methyl]phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-yl]methanol 23m (3.30 g, 4.26 mmol) in dichloromethane (70 mL) was added trifluoroacetic acid (1.26 mL, 17.03 mmol) at 0° C. The mixture was warmed up to room temperature and stirred for 12 hours. The reaction mixture was neutralized with saturated aqueous sodium bicarbonate to pH 7 and 40 mL of water was added, and then the mixture was partitioned. The aqueous layer was extracted with dichloromethane (20 mL×3). The combined organic layers were dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=10/1 to give the title compound 23n as yellow oil (1.62 g, 50%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, CDCl3) δ(ppm): 7.36 (m, 13H), 7.20 (m, 3H), 6.92 (m, 2H), 6.66 (m, 1H), 6.53 (m, 1H), 4.88 (m, 3H), 4.78 (d, 1H), 4.31 (m, 2H), 4.06 (m, 5H), 3.98 (d, 1H), 3.89 (d, 1H), 3.83 (d, 1H), 3.72 (m, 3H), 1.45 (t, 3H).

Provenance & Evidence