Technology Process of 1-(4-(2-chloro-5-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)benzyl)phenyl)ethanone O-methyl oxime
There total 12 articles about 1-(4-(2-chloro-5-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)benzyl)phenyl)ethanone O-methyl oxime which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
pyridine; sodium acetate;
In
ethanol;
for 5h;
Inert atmosphere;
Reflux;
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: zinc(II) oxide / 1 h / 60 °C
2.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C
3.1: tetrakis(triphenylphosphine) palladium(0); 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl-formamide / 3 h / 150 °C
4.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 1 h / 0 - 20 °C
5.1: toluene; diethyl ether; tetrahydrofuran / 12 h / 90 °C
5.2: 20 °C
6.1: sodium acetate; pyridine / ethanol / 5 h / Inert atmosphere; Reflux
With
pyridine; lithium hydroxide monohydrate; water; sodium acetate; triethylamine; zinc(II) oxide;
1,1'-bis-(diphenylphosphino)ferrocene; tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C
1.2: 18 h / -78 - 20 °C
2.1: water; acetic acid / 22 h / 110 °C
2.2: 16 h / 20 °C
3.1: hydrogen bromide; acetic acid / 1 h / 20 °C
4.1: zinc(II) oxide / 1 h / 60 °C
5.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C
6.1: N-ethyl-N,N-diisopropylamine / copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 20 h / 100 °C / Inert atmosphere; Sealed vessel
7.1: formic acid / 2 h / 100 °C
8.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 1 h / 0 - 20 °C
9.1: sodium acetate; pyridine / ethanol / 5 h / Inert atmosphere; Reflux
With
pyridine; n-butyllithium; formic acid; lithium hydroxide monohydrate; water; hydrogen bromide; sodium acetate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; zinc(II) oxide;
bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide;
6.1: Sonogashira Coupling;
