Technology Process of (3S,4S,5R)-ethyl 3-chloro-4,5-bis(formyloxy)cyclohex-1-ene-1-carboxylate
There total 1 articles about (3S,4S,5R)-ethyl 3-chloro-4,5-bis(formyloxy)cyclohex-1-ene-1-carboxylate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
N,N-dimethyl-formamide;
With
thionyl chloride;
at 20 ℃;
for 0.5h;
(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid ethyl ester;
at 0 - 20 ℃;
regioselective reaction;
DOI:10.1002/ejoc.201300804
- Guidance literature:
-
Multi-step reaction with 12 steps
1: potassium carbonate / ethanol / 20 h / 20 °C
2: triethylamine / dichloromethane / 1 h / 0 °C
3: trifluoroacetic acid; water / 8 h / 20 °C
4: sodium azide; acetic acid / dimethyl sulfoxide / 2 h / 85 °C
5: dmap; triethylamine / dichloromethane / 5 h / 20 °C
6: diisobutylaluminium hydride / dichloromethane; hexane / 1 h / -10 °C
7: dmap; triethylamine / ethyl acetate / 1 h / 0 °C
8: water; ruthenium trichloride; sodium periodate / acetonitrile / 4 h / 20 °C
9: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C
10: dmap; triethylamine / tetrahydrofuran / 1 h / 0 °C
11: ammonium hydroxide / methanol / 25 h / Reflux
12: palladium 10% on activated carbon; hydrogen / methanol; water / 24 h / 20 °C
With
dmap; ruthenium trichloride; ammonium hydroxide; sodium periodate; sodium azide; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; water; hydrogen; diisobutylaluminium hydride; potassium carbonate; acetic acid; triethylamine; trifluoroacetic acid;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; acetonitrile;
DOI:10.1002/ejoc.201300804
- Guidance literature:
-
Multi-step reaction with 6 steps
1: potassium carbonate / ethanol / 20 h / 20 °C
2: triethylamine / dichloromethane / 1 h / 0 °C
3: trifluoroacetic acid; water / 8 h / 20 °C
4: sodium azide / ethanol / 3 h / Reflux
5: dmap; triethylamine / dichloromethane / 5 h / 20 °C
6: diisobutylaluminium hydride / dichloromethane; hexane / 1 h / -10 °C
With
dmap; sodium azide; water; diisobutylaluminium hydride; potassium carbonate; triethylamine; trifluoroacetic acid;
In
ethanol; hexane; dichloromethane;
DOI:10.1002/ejoc.201300804
