反应详情

温度

-78 °C

Oxalyl chloride was dissolved in 5 mL methylene chloride and cooled to −78° C., followed by dropwise addition of 3 ml solution of dimethyl sulfoxide ((0.26 mL, 3.59 mmol) in methylene chloride. The reaction mixture was stirred for 15 minutes, before 5 mL solution of [(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(2,3-difluoro-4-methoxy-phenyl)methyl]phenyl]-6-methoxy-tetrahydropyran-2-yl]methanol 2j (1.25 g, 1.71 mmol) in methylene chloride was dropwise added. The mixture was stirred for 40 minutes. The triethylamine (1.19 mL, 8.55 mmol) was dropwise added, before the reaction mixture was warmed to room temperature and stirred for 1.5 hours. Thereafter, the reaction mixture was washed with 5 mL 1 M hydrochloric acid and the organic extract was collected, 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-[(2,3-difluoro-4-methoxy-phenyl)methyl]phenyl]-6-methoxy-tetrahydropyran-2-carbaldehyde 2k (1.24 g, yellow solid), which was used in the next step without purification.

1. additionwas dropwise added
2. temperaturewas warmed to room temperature
3. stirringstirred for 1.5 hours
4. washThereafter, the reaction mixture was washed with 5 mL 1 M hydrochloric acid
5. extractionthe organic extract
6. customwas collected
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationThe filtrate was concentrated under reduced pressure