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

Participants

Reaction Steps

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[[4-[2-(cyclopropoxy)ethoxy]phenyl]methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol 1a (Prepared according to the method in WO2010022313) (3.0 g, 6.06 mmol) was dissolved in 20 mL pyridine, followed by addition of 4-dimethylamino pyridine (148 mg, 1.21 mmol) and TBSCl (1.1 g, 7.27 mmol) in turn. The reaction mixture was stirred for 16 hours, then concentrated under reduced pressure. The residue was dissolved in 100 mL ethyl acetate and 100 mL water and partitioned. The aqueous phase was extracted with ethyl acetate (100 mL), and the organic layer was washed with water (50 mL), combined, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography with elution system A to obtain the title compound (2S,3R,4S,5S,6R)-6-[(tert-butyl(dimethyl)silyl)oxymethyl]-2-[4-chloro-3-[[4-[2-(cyclopropoxy)ethoxy]phenyl]methyl]phenyl]-2-methoxy-tetrahydropyran-3,4,5-triol 1b (3.0 g, yellow solid), yield: 81.1%. 1H NMR (400 MHz, CD3OD): δ 7.50 (dd, 1H), 7.38 (m, 2H), 7.08 (d, 2H), 6.82 (d, 2H), 4.04 (m, 5H), 3.88 (m, 1H), 3.82 (m, 2H), 3.75 (m, 1H), 3.59 (m, 1H), 3.40 (m, 2H), 3.07 (m, 1H), 3.06 (s, 3H), 0.90 (s, 9H), 0.53 (m, 4H), 0.10 (s, 3H), 0.07 (s, 3H).

Provenance & Evidence