Benzyl Bromide → [[(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]methoxy]trimethyl-silane

Temperatur

0 °C

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(2,3-difluoro-4-methoxy-phenyl)methyl]phenyl]-2-methoxy-6-(trimethylsilyloxymethyl)tetrahydropyran-3,4,5-triol 2h (1.63 g, 2.84 mmol) was dissolved in 30 mL DMF and cooled to 0° C., followed by addition of 60% NaH (570 mg, 14.2 mmol). Then the reaction mixture was warmed to room temperature and stirred for 45 minutes. Thereafter, benzyl bromide (1.7 mL, 14.2 mmol) was added before the reaction mixture was stirred overnight. The reaction mixture was concentrated under reduced pressure after 5 mL methanol were added. After 150 mL ethyl acetate and 50 mL water were added into the residue, the resulting residue was partitioned and the organic extract was washed with water (50 mL), combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound [[(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]methoxy]trimethyl-silane 21 (2.4 g, yellow grease), with yield: 100%.

1. temperatureThen the reaction mixture was warmed to room temperature
2. stirringwas stirred overnight
3. concentrationThe reaction mixture was concentrated under reduced pressure after 5 mL methanol
4. additionwere added
5. additionAfter 150 mL ethyl acetate and 50 mL water were added into the residue
6. customthe resulting residue was partitioned
7. extractionthe organic extract
8. washwas washed with water (50 mL)
9. dry with materialdried over anhydrous magnesium sulfate
10. filtrationfiltered
11. concentrationThe filtrate was concentrated under reduced pressure

ORD-Eintrag

ord-9a980bf3e03f443fa39c523854b64d8b

Quelldatensatz

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08609622B2