Technology Process of (2S,3S,4R,5S,6S)-2-(4-chloro-3-(4-((trimethylsilyl)ethynyl)benzyl)phenyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate
There total 7 articles about (2S,3S,4R,5S,6S)-2-(4-chloro-3-(4-((trimethylsilyl)ethynyl)benzyl)phenyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
N-ethyl-N,N-diisopropylamine;
bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide;
In
N,N-dimethyl-formamide;
at 100 ℃;
for 20h;
Inert atmosphere;
Sealed vessel;
- Guidance literature:
-
Multi-step reaction with 6 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
With
n-butyllithium; water; hydrogen bromide; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; zinc(II) oxide;
bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide;
In
tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
6.1: Sonogashira Coupling;
- Guidance literature:
-
Multi-step reaction with 6 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
With
n-butyllithium; water; hydrogen bromide; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; zinc(II) oxide;
bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide;
In
tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
6.1: Sonogashira Coupling;