Technology Process of (6R,7R,8R,8aS)-6,7,8-tris(benzyloxy)hexahydroindolizin-3(5H)-one
There total 29 articles about (6R,7R,8R,8aS)-6,7,8-tris(benzyloxy)hexahydroindolizin-3(5H)-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
benzyl (2S,3R,4R,5R)-3,4,5-tris(benzyloxy)-2-(hydroxymethyl)piperidine-1-carboxylate;
With
pyridine; chromium(VI) oxide; acetic anhydride;
ethyl (triphenylphosphoranylidene)acetate;
In
dichloromethane;
for 6h;
Further stages;
Reflux;
DOI:10.1002/ejoc.201001171
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / 0 - 20 °C
2.1: sodium hydrogencarbonate / ethyl acetate / 4 h / 0 °C
3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C
3.2: 2 h
4.1: Grubbs catalyst first generation / dichloromethane / 12 h / 20 °C
5.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 20 °C
6.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 - 20 °C
6.2: 8 h / 20 °C
7.1: trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C
8.1: pyridinium chlorochromate / dichloromethane / 4 h / 0 °C
9.1: dichloromethane / 6 h / Reflux
10.1: palladium 10% on activated carbon; hydrogen / ethanol / 12 h / 760.05 Torr
11.1: sodium acetate / ethanol / 10 h / Reflux
With
Grubbs catalyst first generation; osmium(VIII) oxide; lithium aluminium tetrahydride; palladium 10% on activated carbon; hydrogen; sodium acetate; sodium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; pyridinium chlorochromate; trifluoroacetic acid;
In
tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; mineral oil; tert-butyl alcohol;
9.1: Wittig reaction;
DOI:10.1002/ejoc.201001171
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: sodium azide / N,N-dimethyl-formamide / 6 h / 120 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / 0 - 20 °C
3.1: sodium hydrogencarbonate / ethyl acetate / 4 h / 0 °C
4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C
4.2: 2 h
5.1: Grubbs catalyst first generation / dichloromethane / 12 h / 20 °C
6.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 20 °C
7.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 - 20 °C
7.2: 8 h / 20 °C
8.1: trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C
9.1: pyridinium chlorochromate / dichloromethane / 4 h / 0 °C
10.1: dichloromethane / 6 h / Reflux
11.1: palladium 10% on activated carbon; hydrogen / ethanol / 12 h / 760.05 Torr
12.1: sodium acetate / ethanol / 10 h / Reflux
With
Grubbs catalyst first generation; osmium(VIII) oxide; lithium aluminium tetrahydride; sodium azide; palladium 10% on activated carbon; hydrogen; sodium acetate; sodium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; pyridinium chlorochromate; trifluoroacetic acid;
In
tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; mineral oil; tert-butyl alcohol;
10.1: Wittig reaction;
DOI:10.1002/ejoc.201001171
