Technology Process of (4aR,5S,6R,7S)-tert-butyl 6-benzyloxy-5-(6-(tert-butyldiphenylsilyloxy)-2-oxohexyl)-7-methyl-2,3,4,4a,5,6,7,8-octahydroquinoline-4a-carboxylate
There total 18 articles about (4aR,5S,6R,7S)-tert-butyl 6-benzyloxy-5-(6-(tert-butyldiphenylsilyloxy)-2-oxohexyl)-7-methyl-2,3,4,4a,5,6,7,8-octahydroquinoline-4a-carboxylate which
guide to synthetic route it.
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synthetic route:
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869385-14-8
(4aR,5S,6R,7S)-tert-butyl 6-benzyloxy-5-(6-(tert-butyldiphenylsilyloxy)-2-oxohexyl)-7-methyl-2,3,4,4a,5,6,7,8-octahydroquinoline-4a-carboxylate
- Guidance literature:
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With
hydrogen; nickel;
In
ethanol;
at 20 ℃;
for 38h;
DOI:10.1002/anie.200502296
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869385-14-8
(4aR,5S,6R,7S)-tert-butyl 6-benzyloxy-5-(6-(tert-butyldiphenylsilyloxy)-2-oxohexyl)-7-methyl-2,3,4,4a,5,6,7,8-octahydroquinoline-4a-carboxylate
- Guidance literature:
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Multi-step reaction with 12 steps
1.1: Et3N; DMAP / CH2Cl2 / 4 h / 20 °C
2.1: 4.23 g / dimethylsulfoxide / 24 h / 50 °C
3.1: O3 / methanol; CH2Cl2 / -78 °C
3.2: Me2S / methanol; CH2Cl2 / 3 h / 20 °C
4.1: 7.1 g / NaH / tetrahydrofuran / 2 h / -78 - -20 °C
5.1: L-selectride / tetrahydrofuran / 1.5 h / -78 °C
6.1: 5.25 g / imidazole / dimethylformamide / 30 h / 20 °C
7.1: 83 percent / Dibal-H / CH2Cl2 / 1.5 h / -78 - -50 °C
8.1: LDA / tetrahydrofuran; hexane / 1.17 h / -78 - 0 °C
9.1: PPTS / ethanol / 1.25 h / 20 °C
9.2: Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 20 °C
10.1: 96 percent / Cs2CO3 / ethanol / -78 - 0 °C
11.1: Bu4NOH*30H2O / acetonitrile / 5 h / 20 °C
12.1: 74 percent / Raney nickel; H2 / ethanol / 38 h / 20 °C
With
1H-imidazole; dmap; tetra(n-butyl)ammonium hydroxide; hydrogen; pyridinium p-toluenesulfonate; L-Selectride; nickel; sodium hydride; diisobutylaluminium hydride; caesium carbonate; ozone; triethylamine; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;
4.1: Horner-Wadsworth-Emmons reaction / 9.2: Dess-Martin oxidation / 11.1: Michael addition;
DOI:10.1002/anie.200502296
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-
869385-14-8
(4aR,5S,6R,7S)-tert-butyl 6-benzyloxy-5-(6-(tert-butyldiphenylsilyloxy)-2-oxohexyl)-7-methyl-2,3,4,4a,5,6,7,8-octahydroquinoline-4a-carboxylate
- Guidance literature:
-
Multi-step reaction with 13 steps
1.1: 76 percent / Dibal-H / CH2Cl2 / 36 h / -78 - -35 °C
2.1: Et3N; DMAP / CH2Cl2 / 4 h / 20 °C
3.1: 4.23 g / dimethylsulfoxide / 24 h / 50 °C
4.1: O3 / methanol; CH2Cl2 / -78 °C
4.2: Me2S / methanol; CH2Cl2 / 3 h / 20 °C
5.1: 7.1 g / NaH / tetrahydrofuran / 2 h / -78 - -20 °C
6.1: L-selectride / tetrahydrofuran / 1.5 h / -78 °C
7.1: 5.25 g / imidazole / dimethylformamide / 30 h / 20 °C
8.1: 83 percent / Dibal-H / CH2Cl2 / 1.5 h / -78 - -50 °C
9.1: LDA / tetrahydrofuran; hexane / 1.17 h / -78 - 0 °C
10.1: PPTS / ethanol / 1.25 h / 20 °C
10.2: Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 20 °C
11.1: 96 percent / Cs2CO3 / ethanol / -78 - 0 °C
12.1: Bu4NOH*30H2O / acetonitrile / 5 h / 20 °C
13.1: 74 percent / Raney nickel; H2 / ethanol / 38 h / 20 °C
With
1H-imidazole; dmap; tetra(n-butyl)ammonium hydroxide; hydrogen; pyridinium p-toluenesulfonate; L-Selectride; nickel; sodium hydride; diisobutylaluminium hydride; caesium carbonate; ozone; triethylamine; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;
5.1: Horner-Wadsworth-Emmons reaction / 10.2: Dess-Martin oxidation / 12.1: Michael addition;
DOI:10.1002/anie.200502296