Dimethyl Sulfoxide → (2S,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[4-(trifluoromethoxy)phenyl]methyl]phenyl]-6-methoxy-tetrahydropyran-2-carbaldehyde

온도

-78 °C

Oxalyl chloride (0.21 mL, 2.45 mmol) was dissolved in 5 mL dichloromethane and cooled to −78° C. The mixture was stirred for 15 minutes after 5 mL solution of dimethyl sulfoxide (0.24 mL, 3.26 mmol) in dichloromethane were added. Then 10 mL solution of [(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[4-(trifluoromethoxy)phenyl]methyl]phenyl]-6-methoxy-tetrahydropyran-2-yl]methanol 6m (1.22 g, 1.63 mmol) in dichloromethane were added before the mixture was stirred for 40 minutes. Then the reaction mixture was warmed and stirred for 1.5 hours at room temperature after triethylamine (1.18 mL, 8.15 mmol) was added and partitioned after 10 mL 1 M hydrochloric acid were added. The organic extract was washed with saturated sodium chloride solution (10 mL×2) and 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-(trifluoromethoxy)phenyl]methyl]phenyl]-6-methoxy-tetrahydropyran-2-carbaldehyde 6n (1.21 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 added
4. custompartitioned after 10 mL 1 M hydrochloric acid
5. additionwere added
6. extractionThe organic extract
7. washwas washed with saturated sodium chloride solution (10 mL×2)
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationfiltered
10. concentrationThe filtrate was concentrated under reduced pressure

ORD 기록

ord-b543864909d242b2afb2d67cf331302b

출처 데이터셋

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08609622B2