Imidazole → (2S,3R,4S,5S,6R)-6-[(tert-butyl(dimethyl)silyl)oxymethyl]-2-[4-chloro-3-[[4-(trifluoromethoxy)phenyl]methyl]phenyl]-2-methoxy-tetrahydropyran-3,4,5-triol

Participants

Reaction Steps

To a solution of (2S,3R,4S,5S,6R)-2-[4-chloro-3-[[4-(trifluoromethoxy)phenyl]methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol 15h (1.0 g, 2.09 mmol) in dichloromethane (15 mL) were added imidazole (0.57 g, 8.39 mmol), tert-butyldimethylsilyl chloride (0.63 g, 4.19 mmol) and 4-dimethylaminopyridine (26 mg, 0.21 mmol) in turn at 0° C. The mixture was warmed up to room temperature and stirred for 1.5 hours. The reaction mixture was adjusted with saturated aqueous sodium bicarbonate to pH 7 and partitioned. The aqueous layer was extracted with dichloromethane (20 mL×2). The combined organic layers were washed with saturated brine (20 mL×2), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound 15i as yellow oil (1.37 g, 100%). This material was not further purified.

Provenance & Evidence