Technology Process of (2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-((3-ethyloxetan-3-yl)methoxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
There total 10 articles about (2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-((3-ethyloxetan-3-yl)methoxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: aluminum (III) chloride / dichloromethane / 12 h / 20 °C / Inert atmosphere
2.1: triethylsilane; boron trifluoride diethyl etherate / diethyl ether; dichloromethane; acetonitrile / 16 h / 20 °C / Inert atmosphere
3.1: caesium carbonate / N,N-dimethyl-formamide / 100 °C
4.1: tert.-butyl lithium / tetrahydrofuran; toluene / 2 h / -78 °C
4.2: 3 h / 20 °C
With
triethylsilane; boron trifluoride diethyl etherate; tert.-butyl lithium; caesium carbonate;
aluminum (III) chloride;
In
tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
- Guidance literature:
-
3-((4-(5-bromo-2-chlorobenzyl)phenoxy)methyl)-3-ethyloxetane; (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one;
With
tert.-butyl lithium;
In
tetrahydrofuran; toluene;
at -78 ℃;
for 2h;
With
methanesulfonic acid;
In
tetrahydrofuran; methanol; toluene;
at 20 ℃;
for 3h;
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 12 h / 20 °C
2.1: aluminum (III) chloride / dichloromethane / 1 h / 0 °C
3.1: aluminum (III) chloride / dichloromethane / 12 h / 20 °C / Inert atmosphere
4.1: triethylsilane; boron trifluoride diethyl etherate / diethyl ether; dichloromethane; acetonitrile / 16 h / 20 °C / Inert atmosphere
5.1: caesium carbonate / N,N-dimethyl-formamide / 100 °C
6.1: tert.-butyl lithium / tetrahydrofuran; toluene / 2 h / -78 °C
6.2: 3 h / 20 °C
With
triethylsilane; thionyl chloride; boron trifluoride diethyl etherate; tert.-butyl lithium; caesium carbonate;
aluminum (III) chloride;
In
tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;