Technology Process of (3R,4S,5S,6R)-2-(4-chloro-3-((4-(cyclopropyl-1-d)phenyl)methyl-d2)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
There total 10 articles about (3R,4S,5S,6R)-2-(4-chloro-3-((4-(cyclopropyl-1-d)phenyl)methyl-d2)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:
-
4-bromo-1-chloro-2-((4-(cyclopropyl-1-d)phenyl)methyl-d2)benzene;
With
n-butyllithium;
In
tetrahydrofuran; hexane; toluene;
at -78 ℃;
Inert atmosphere;
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one;
In
tetrahydrofuran; hexane; toluene;
at -78 ℃;
for 1h;
methanol;
With
toluene-4-sulfonic acid;
In
water;
at 0 - 25 ℃;
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: aluminum (III) chloride / dichloromethane / 0 - 25 °C
2.1: trifluorormethanesulfonic acid; trifluoroacetic acid / 5 h / 25 °C
3.1: ammonium chloride; zinc / methanol / 8 h / Reflux
4.1: tetrabutylammonium bisulfate; water-d2; sodium hydride / hexane; mineral oil / 0 - 25 °C
5.1: n-butyllithium / tetrahydrofuran; hexane; toluene / -78 °C / Inert atmosphere
5.2: 1 h / -78 °C
5.3: 0 - 25 °C
With
aluminum (III) chloride; n-butyllithium; trifluorormethanesulfonic acid; tetrabutylammonium bisulfate; water-d2; sodium hydride; ammonium chloride; trifluoroacetic acid; zinc;
In
tetrahydrofuran; methanol; hexane; dichloromethane; toluene; mineral oil;
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: N-benzyl-N,N,N-triethylammonium chloride; potassium hydroxide / dichloromethane / 19 h / Reflux
1.2: 5 h
1.3: 12 h / Reflux
2.1: aluminum (III) chloride / dichloromethane / 0 - 25 °C
3.1: trifluorormethanesulfonic acid; trifluoroacetic acid / 5 h / 25 °C
4.1: ammonium chloride; zinc / methanol / 8 h / Reflux
5.1: tetrabutylammonium bisulfate; water-d2; sodium hydride / hexane; mineral oil / 0 - 25 °C
6.1: n-butyllithium / tetrahydrofuran; hexane; toluene / -78 °C / Inert atmosphere
6.2: 1 h / -78 °C
6.3: 0 - 25 °C
With
aluminum (III) chloride; n-butyllithium; trifluorormethanesulfonic acid; tetrabutylammonium bisulfate; N-benzyl-N,N,N-triethylammonium chloride; water-d2; sodium hydride; ammonium chloride; trifluoroacetic acid; potassium hydroxide; zinc;
In
tetrahydrofuran; methanol; hexane; dichloromethane; toluene; mineral oil;