Imidazole → (2S,3R,4S,5S,6R)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-[4-chloro-3-[(2,3-difluoro-4-methoxy-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-[(2,3-difluoro-4-methoxy-phenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol 21h (1.12 g, 2.38 mmol) in dichloromethane (20 mL) were added tert-butyldimethylsilyl chloride (0.54 g, 3.58 mmol) and imidazole (0.49 g, 7.16 mmol) in turn at room temperature. The mixture was stirred at room temperature for 3 hours. The mixture was partitioned between dichloromethane (40 mL) and water (40 mL). The organic layer was washed with saturated aqueous sodium chloride (30 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound 21i as yellow oil (1.37 g, 100%).

Provenance & Evidence