反应详情

温度

0 °C

To a solution of (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 15i (1.37 g, 1.69 mmol) in anhydrous tetrahydrofuran (15 mL) was added sodium hydride (0.20 g, 8.45 mmol, 60% dispersion in Mineral oil) at 0° C. The mixture was stirred at 0° C. for 15 min, and then benzyl bromide (1.45 g, 8.45 mmol) and tetrabutylammonium iodide (0.06 g, 0.17 mmol) were added in turn. The mixture was further stirred at room temperature for 20 hours. The reaction mixture was quenched with water (10 mL) and extracted with ethyl acetate (20 mL). The aqueous layer was extracted with ethyl acetate (20 mL×3). The combined organic layers were washed with saturated brine (20 mL×3), dried over anhydrous sodium sulfate, filtered. The filtrate was concentrated in vacuo to give the title compound 15j as yellow oil (1.9 g, 100%). This material was not further purified.

1. stirringThe mixture was further stirred at room temperature for 20 hours
2. customThe reaction mixture was quenched with water (10 mL)
3. extractionextracted with ethyl acetate (20 mL)
4. extractionThe aqueous layer was extracted with ethyl acetate (20 mL×3)
5. washThe combined organic layers were washed with saturated brine (20 mL×3)
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationThe filtrate was concentrated in vacuo