Technology Process of [(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[dideuterio-(4-ethoxy-3-fluorophenyl)methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]methanol
There total 14 articles about [(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[dideuterio-(4-ethoxy-3-fluorophenyl)methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]methanol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
trifluoroacetic acid;
In
dichloromethane;
at -10 - 20 ℃;
for 2h;
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: aluminum (III) chloride / dichloromethane / 16 h / 0 °C
2.1: aluminum (III) chloride; trifluoroacetic acid / tetrahydrofuran / 2 h / 20 °C / Cooling with ice
3.1: trifluoroacetic acid / 3 h
4.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 °C
4.2: 2 h / -78 °C
4.3: 16 h / 20 °C
5.1: dmap; 1H-imidazole / dichloromethane / 16 h
6.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.67 h / 20 °C / Cooling with ice
6.2: 3 h
7.1: methanol / 1 h
8.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 2.5 h / -78 - 20 °C
9.1: sodium hydroxide / 1,4-dioxane / 6 h / 70 °C
10.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 2 h
11.1: trifluoroacetic acid / dichloromethane / 2 h / -10 - 20 °C
With
1H-imidazole; methanol; dmap; aluminum (III) chloride; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; sodium hydride; trifluoroacetic acid; sodium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; mineral oil;
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: potassium carbonate / acetone / 5 h / Reflux
2.1: aluminum (III) chloride / dichloromethane / 16 h / 0 °C
3.1: aluminum (III) chloride; trifluoroacetic acid / tetrahydrofuran / 2 h / 20 °C / Cooling with ice
4.1: trifluoroacetic acid / 3 h
5.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 °C
5.2: 2 h / -78 °C
5.3: 16 h / 20 °C
6.1: dmap; 1H-imidazole / dichloromethane / 16 h
7.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.67 h / 20 °C / Cooling with ice
7.2: 3 h
8.1: methanol / 1 h
9.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 2.5 h / -78 - 20 °C
10.1: sodium hydroxide / 1,4-dioxane / 6 h / 70 °C
11.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 2 h
12.1: trifluoroacetic acid / dichloromethane / 2 h / -10 - 20 °C
With
1H-imidazole; methanol; dmap; aluminum (III) chloride; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; sodium hydride; potassium carbonate; trifluoroacetic acid; sodium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; mineral oil;
![[(3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[dideuterio-(4-ethoxy-3-fluorophenyl)methyl]phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-yl]methanol](/Databaselist/images/loading.webp)
