1,2-Dichlorobenzene → (1S,2S,3S,4R,5S)-5-[4-chloro-3-[(2,3-difluoro-4-methoxy-phenyl)methyl]phenyl]-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol

[(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[(2,3-difluoro-4-methoxy-phenyl)methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]methanol 2p (350 mg, 0.48 mmol) was dissolved in 10 mL of mixed solution (THF and MeOH, v:v=1:1), followed by addition of o-dichlorobenzene (0.55 mL, 4.8 mmol) and Palladium/carbon (300 mg, 10%) in turn. The mixture was exchanged with H2 three times and stirred for 3 hours, filtered with silica gel and the filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel chromatography with elution system A to obtain the title compound (1S,2S,3S,4R,5S)-5-[4-chloro-3-[(2,3-difluoro-4-methoxy-phenyl)methyl]phenyl]-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol 2 (210 mg, white solid), yield: 95.5%. MS m/z (ESI): 459.1 [M+1];

1. filtrationfiltered with silica gel
2. concentrationthe filtrate was concentrated under reduced pressure
3. customthe resulting residue was purified by silica gel chromatography with elution system

ORD 기록

ord-388a612bc90f4b0a82cd6f26c37a3ef7

출처 데이터셋

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08609622B2