Technology Process of tert-butyl-(3R,5S,6E)-7-[6,7,8-trifluoro-4-(4-fluorophenylthio)quinoline-3-yl]-3,5-dihydroxyhept-6-enoate
There total 7 articles about tert-butyl-(3R,5S,6E)-7-[6,7,8-trifluoro-4-(4-fluorophenylthio)quinoline-3-yl]-3,5-dihydroxyhept-6-enoate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: trichlorophosphate / toluene / 2 h / Reflux; Large scale
2.1: sodium hydrogencarbonate / dichloromethane / 19 h / Reflux; Large scale
3.1: diisobutylaluminium hydride / toluene / 7 h / -5 - 0 °C / Inert atmosphere; Large scale
4.1: phosphorus tribromide / dichloromethane / 2 h / 0 - 20 °C
5.1: toluene / 2 h / Resolution of racemate
6.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C / Inert atmosphere
6.2: 3 h / 0 - 20 °C / Inert atmosphere
7.1: hydrogenchloride; water / tetrahydrofuran
With
2,2,6,6-tetramethyl-piperidine; hydrogenchloride; n-butyllithium; water; phosphorus tribromide; diisobutylaluminium hydride; sodium hydrogencarbonate; trichlorophosphate;
In
tetrahydrofuran; hexane; dichloromethane; toluene;
6.2: |Wittig-Horner Reaction;
DOI:10.1021/op400060z
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: sodium hydrogencarbonate / dichloromethane / 19 h / Reflux; Large scale
2.1: diisobutylaluminium hydride / toluene / 7 h / -5 - 0 °C / Inert atmosphere; Large scale
3.1: phosphorus tribromide / dichloromethane / 2 h / 0 - 20 °C
4.1: toluene / 2 h / Resolution of racemate
5.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C / Inert atmosphere
5.2: 3 h / 0 - 20 °C / Inert atmosphere
6.1: hydrogenchloride; water / tetrahydrofuran
With
2,2,6,6-tetramethyl-piperidine; hydrogenchloride; n-butyllithium; water; phosphorus tribromide; diisobutylaluminium hydride; sodium hydrogencarbonate;
In
tetrahydrofuran; hexane; dichloromethane; toluene;
5.2: |Wittig-Horner Reaction;
DOI:10.1021/op400060z
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: diisobutylaluminium hydride / toluene / 7 h / -5 - 0 °C / Inert atmosphere; Large scale
2.1: phosphorus tribromide / dichloromethane / 2 h / 0 - 20 °C
3.1: toluene / 2 h / Resolution of racemate
4.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / hexane; 2-methyltetrahydrofuran / 1 h / 0 °C / Inert atmosphere
4.2: 3 h / 0 - 20 °C / Inert atmosphere
5.1: hydrogenchloride; water / tetrahydrofuran
With
2,2,6,6-tetramethyl-piperidine; hydrogenchloride; n-butyllithium; water; phosphorus tribromide; diisobutylaluminium hydride;
In
tetrahydrofuran; 2-methyltetrahydrofuran; hexane; dichloromethane; toluene;
4.2: |Wittig-Horner Reaction;
DOI:10.1021/op400060z
