Technology Process of (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
There total 14 articles about (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 which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
palladium 10% on activated carbon; hydrogen;
In
tetrahydrofuran; methanol; dichloromethane;
for 3h;
- Guidance literature:
-
Multi-step reaction with 13 steps
1.1: thionyl chloride / toluene; N,N-dimethyl-formamide / 5 h / 0 - 100 °C
2.1: aluminum (III) chloride / dichloromethane / 16 h / 0 °C
3.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 0.5 h
4.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 16 h
5.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 1 h / -78 °C
5.2: 3 h / -78 °C
6.1: pyridine; dmap / pyridine; ethyl acetate / 16 h
7.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.75 h / 0 - 20 °C
8.1: methanol / 1 h
9.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 0.67 h / -78 °C
9.2: 1.5 h / 20 °C
10.1: sodium hydroxide; water / 1,4-dioxane / 70 °C
11.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 0.33 h
12.1: trifluoroacetic acid / dichloromethane / 1.5 h
13.1: palladium 10% on activated carbon; hydrogen / dichloromethane; tetrahydrofuran; methanol / 3 h
With
pyridine; methanol; triethylsilane; dmap; aluminum (III) chloride; sodium tetrahydroborate; n-butyllithium; thionyl chloride; oxalyl dichloride; palladium 10% on activated carbon; boron trifluoride diethyl etherate; water; hydrogen; sodium hydride; trifluoroacetic acid; sodium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; pyridine; methanol; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; mineral oil;
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: aluminum (III) chloride / dichloromethane / 16 h / 0 °C
2.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 0.5 h
3.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 16 h
4.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 1 h / -78 °C
4.2: 3 h / -78 °C
5.1: pyridine; dmap / pyridine; ethyl acetate / 16 h
6.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.75 h / 0 - 20 °C
7.1: methanol / 1 h
8.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 0.67 h / -78 °C
8.2: 1.5 h / 20 °C
9.1: sodium hydroxide; water / 1,4-dioxane / 70 °C
10.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 0.33 h
11.1: trifluoroacetic acid / dichloromethane / 1.5 h
12.1: palladium 10% on activated carbon; hydrogen / dichloromethane; tetrahydrofuran; methanol / 3 h
With
pyridine; methanol; triethylsilane; dmap; aluminum (III) chloride; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; palladium 10% on activated carbon; boron trifluoride diethyl etherate; water; hydrogen; sodium hydride; trifluoroacetic acid; sodium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; pyridine; methanol; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; mineral oil;
![[(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](/Databaselist/images/loading.webp)
