Technology Process of (1S,2S,3S,4R,5S)-5-[4-chloro-3-[dideuterio-(4-ethoxy-3-fluoro-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-[dideuterio-(4-ethoxy-3-fluoro-phenyl)methyl]phenyl]-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
- Guidance literature:
-
Multi-step reaction with 12 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
12.1: palladium 10% on activated carbon; hydrogen / dichloromethane; tetrahydrofuran; methanol / 3 h
With
1H-imidazole; methanol; dmap; aluminum (III) chloride; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; palladium 10% on activated carbon; hydrogen; 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 13 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
13.1: palladium 10% on activated carbon; hydrogen / dichloromethane; tetrahydrofuran; methanol / 3 h
With
1H-imidazole; methanol; dmap; aluminum (III) chloride; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; palladium 10% on activated carbon; hydrogen; 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;
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: aluminum (III) chloride; trifluoroacetic acid / tetrahydrofuran / 2 h / 20 °C / Cooling with ice
2.1: trifluoroacetic acid / 3 h
3.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 °C
3.2: 2 h / -78 °C
3.3: 16 h / 20 °C
4.1: dmap; 1H-imidazole / dichloromethane / 16 h
5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.67 h / 20 °C / Cooling with ice
5.2: 3 h
6.1: methanol / 1 h
7.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 2.5 h / -78 - 20 °C
8.1: sodium hydroxide / 1,4-dioxane / 6 h / 70 °C
9.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 2 h
10.1: trifluoroacetic acid / dichloromethane / 2 h / -10 - 20 °C
11.1: palladium 10% on activated carbon; hydrogen / dichloromethane; tetrahydrofuran; methanol / 3 h
With
1H-imidazole; methanol; dmap; aluminum (III) chloride; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; palladium 10% on activated carbon; hydrogen; sodium hydride; trifluoroacetic acid; sodium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; mineral oil;
