tert-Butyldimethylsilyl chloride → HCID 86685126, compound

Participants

Reaction Steps

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxy-3-fluoro-phenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol 4f (5.7 g, 12.5 mmol) was dissolved in 50 mL pyridine, followed by addition of TBSCl (2.26 g, 15 mmol) and 4-dimethyl-amino pyridine (305 mg, 2.5 mmol) in turn. The reaction mixture was stirred for 16 hours. Thereafter, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in 200 mL ethyl acetate and washed with saturated copper sulfate solution (50 mL×3). The organic extract was combined, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain the title compound (2S,3R,4S,5S,6R)-6-[(tert-butyl(dimethyl)silyl)oxymethyl]-2-[4-chloro-3-[(4-ethoxy-3-fluoro-phenyl)methyl]phenyl]-2-methoxy-tetrahydropyran-3,4,5-triol 4g (7.14 g, colourless grease), which was used directly without purification in the next step.

Provenance & Evidence