tert-Butyldimethylsilyl chloride → HCID 86685157, compound

Participants

Reaction Steps

(2S,3R,4S,5S,6R)-2-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methyl-phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol 9d (1.8 g, 3.8 mmol) was dissolved in 20 mL pyridine, followed by addition of 4-dimethylamino pyridine (93 mg, 0.76 mmol) and TBSCl (686 mg, 4.55 mmol) in turn. The reaction mixture was stirred for 16 hours. Thereafter, the reaction mixture was concentrated under reduced pressure, dissolved in 30 mL ethyl acetate and was partitioned after 30 mL water were added. The aqueous phase was extracted with ethyl acetate (30 mL×3) and the organic extracts were combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel chromatography with elution system A to obtain the title compound (2S,3R,4S,5S,6R)-6-[(tertbutyl(dimethyl)silyl)oxymethyl]-2-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methyl-phenyl]-2-methoxy-tetrahydropyran-3,4,5-triol 9e (2.0 g, orange solid), yield: 89.7%.

Provenance & Evidence