反应详情

温度

-78 °C

Oxalyl chloride (0.16 mL, 1.87 mmol) was dissolved in 5 mL dichloromethane and cooled to −78° C., followed by dropwise addition of dimethyl sulfoxide (0.2 mL, 2.88 mmol) in dichloromethane (3 mL). The reaction mixture was stirred for 15 minutes, before 10 mL solution of [(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[4-(2,2,2-trifluoroethoxy)phenyl]methyl]phenyl]-6-methoxy-tetrahydropyran-2-yl]methanol 7h (1.10 g, 1.44 mmol) in dichloromethane were added and stirred for 40 minutes. Then the reaction mixture was warmed and stirred for 3 hours at room temperature after triethylamine (1.0 mL, 7.21 mmol) was dropwise added. Thereafter, the reaction mixture was partitioned after 5 mL 1 M hydrochloric acid were added, the aqueous phase was extracted with ethyl acetate (10 mL×2) and the organic extracts were combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (2S,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[4-(2,2,2-trifluoroethoxy)phenyl]methyl]phenyl]-6-methoxy-tetrahydropyran-2-carbaldehyde 7i (1.06 g, yellow grease), which was used directly in the next step without purification.

1. additionwere added
2. temperatureThen the reaction mixture was warmed
3. additionwas dropwise added
4. customThereafter, the reaction mixture was partitioned after 5 mL 1 M hydrochloric acid
5. additionwere added
6. extractionthe aqueous phase was extracted with ethyl acetate (10 mL×2)
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationThe filtrate was concentrated under reduced pressure