Technology Process of (2S,3R,4R,5S,6R)-2-(4-chloro-3-((4-(2-(2,2-difluoroethoxy)ethoxy)phenyl)methyl-d2)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol
There total 10 articles about (2S,3R,4R,5S,6R)-2-(4-chloro-3-((4-(2-(2,2-difluoroethoxy)ethoxy)phenyl)methyl-d2)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
caesium carbonate;
In
N,N-dimethyl-formamide;
at 80 ℃;
for 2h;
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: aluminum (III) chloride; sodium borodeuteride / tetrahydrofuran / 5 - 70 °C
2.1: boron tribromide / dichloromethane / -60 - 25 °C
2.2: Cooling with ice
3.1: potassium carbonate / acetone / 20 - 75 °C
4.1: n-butyllithium / tetrahydrofuran; hexane; toluene / -78 - -70 °C
4.2: 5 h / -78 - -70 °C
4.3: 20 °C
5.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 2.5 h / -15 °C
6.1: boron tribromide / dichloromethane / -78 - 0 °C
6.2: Ice water added into reaction
7.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C
With
triethylsilane; aluminum (III) chloride; n-butyllithium; sodium borodeuteride; boron trifluoride diethyl etherate; boron tribromide; potassium carbonate; caesium carbonate;
In
tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 10 h / 20 °C / Industry scale
2.1: aluminum (III) chloride / dichloromethane / -3 - 4 °C / Industry scale
3.1: triethylsilane; trifluorormethanesulfonic acid; trifluoroacetic acid / 14 h / Reflux
4.1: [D]-sodium hydroxide; tetrabutylammonium bisulfate; water-d2 / hexane; mineral oil / 24 h / 25 °C / Sealed tube
4.2: 20 °C
5.1: boron tribromide / dichloromethane / -60 - 25 °C
5.2: Cooling with ice
6.1: potassium carbonate / acetone / 20 - 75 °C
7.1: n-butyllithium / tetrahydrofuran; hexane; toluene / -78 - -70 °C
7.2: 5 h / -78 - -70 °C
7.3: 20 °C
8.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 2.5 h / -15 °C
9.1: boron tribromide / dichloromethane / -78 - 0 °C
9.2: Ice water added into reaction
10.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C
With
triethylsilane; aluminum (III) chloride; n-butyllithium; oxalyl dichloride; [D]-sodium hydroxide; trifluorormethanesulfonic acid; tetrabutylammonium bisulfate; boron trifluoride diethyl etherate; water-d2; boron tribromide; potassium carbonate; caesium carbonate; N,N-dimethyl-formamide; trifluoroacetic acid;
In
tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; mineral oil;