Technology Process of 6-{(1E,3S,5S,6S,7E,9E,11E)-[13-(4-methoxybenzyloxy)-6-(methoxymethoxy)-1,3,5,11-tetramethyltrideca-1,7,9,11-tetraen-1-yl]}-2,2-dimethyl-4H-1,3-dioxen-4-one
There total 18 articles about 6-{(1E,3S,5S,6S,7E,9E,11E)-[13-(4-methoxybenzyloxy)-6-(methoxymethoxy)-1,3,5,11-tetramethyltrideca-1,7,9,11-tetraen-1-yl]}-2,2-dimethyl-4H-1,3-dioxen-4-one which
guide to synthetic route it.
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synthetic route:
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910042-96-5
6-{(1E,3S,5S,6S,7E,9E,11E)-[13-(4-methoxybenzyloxy)-6-(methoxymethoxy)-1,3,5,11-tetramethyltrideca-1,7,9,11-tetraen-1-yl]}-2,2-dimethyl-4H-1,3-dioxen-4-one
- Guidance literature:
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Multi-step reaction with 6 steps
1.1: 86 percent / hydrogen / Pd/C / ethanol / 760 Torr
2.1: 100 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / 0.67 h / -78 - 20 °C
3.1: HMPA; nBuLi / tetrahydrofuran; petroleum ether / 0.17 h / cooling
3.2: 92 percent / tetrahydrofuran; petroleum ether / 1.17 h / -78 - 20 °C
4.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C
5.1: 100 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 20 °C
6.1: LDA / tetrahydrofuran; petroleum ether / -78 - 0 °C
6.2: 78 percent / HMPA / tetrahydrofuran; petroleum ether / -78 - 20 °C
With
N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; dichloromethane; Petroleum ether;
2.1: Swern oxidation / 3.2: Horner-Wadsworth-Emmons olefination / 5.1: Swern oxidation / 6.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/ja0581346
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910042-96-5
6-{(1E,3S,5S,6S,7E,9E,11E)-[13-(4-methoxybenzyloxy)-6-(methoxymethoxy)-1,3,5,11-tetramethyltrideca-1,7,9,11-tetraen-1-yl]}-2,2-dimethyl-4H-1,3-dioxen-4-one
- Guidance literature:
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Multi-step reaction with 7 steps
1.1: 89 percent / iPr2NEt; TBAI / CH2Cl2 / 48 h / 20 °C
2.1: 86 percent / hydrogen / Pd/C / ethanol / 760 Torr
3.1: 100 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / 0.67 h / -78 - 20 °C
4.1: HMPA; nBuLi / tetrahydrofuran; petroleum ether / 0.17 h / cooling
4.2: 92 percent / tetrahydrofuran; petroleum ether / 1.17 h / -78 - 20 °C
5.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C
6.1: 100 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 20 °C
7.1: LDA / tetrahydrofuran; petroleum ether / -78 - 0 °C
7.2: 78 percent / HMPA / tetrahydrofuran; petroleum ether / -78 - 20 °C
With
N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; dichloromethane; Petroleum ether;
3.1: Swern oxidation / 4.2: Horner-Wadsworth-Emmons olefination / 6.1: Swern oxidation / 7.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/ja0581346
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910042-96-5
6-{(1E,3S,5S,6S,7E,9E,11E)-[13-(4-methoxybenzyloxy)-6-(methoxymethoxy)-1,3,5,11-tetramethyltrideca-1,7,9,11-tetraen-1-yl]}-2,2-dimethyl-4H-1,3-dioxen-4-one
- Guidance literature:
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Multi-step reaction with 10 steps
1.1: imidazole / dimethylformamide / 15 h / 20 °C
1.2: DDQ; water / CH2Cl2 / 0.25 h / 20 °C
1.3: 72 percent / NaBH4 / CH2Cl2 / 24 h / 20 °C
2.1: (-)-DET; tBuOOH; 4A MS / Ti(OiPr)4 / CH2Cl2 / 24 h / -40 - -23 °C
2.2: 2.42 g / KH; TBAI / tetrahydrofuran / 0.75 h / 0 - 20 °C
3.1: 78 percent / nBuLi / petroleum ether / 3 h / -30 - 0 °C
4.1: 89 percent / iPr2NEt; TBAI / CH2Cl2 / 48 h / 20 °C
5.1: 86 percent / hydrogen / Pd/C / ethanol / 760 Torr
6.1: 100 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / 0.67 h / -78 - 20 °C
7.1: HMPA; nBuLi / tetrahydrofuran; petroleum ether / 0.17 h / cooling
7.2: 92 percent / tetrahydrofuran; petroleum ether / 1.17 h / -78 - 20 °C
8.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C
9.1: 100 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 20 °C
10.1: LDA / tetrahydrofuran; petroleum ether / -78 - 0 °C
10.2: 78 percent / HMPA / tetrahydrofuran; petroleum ether / -78 - 20 °C
With
1H-imidazole; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide;
titanium(IV) isopropylate; palladium on activated charcoal;
In
tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; Petroleum ether;
6.1: Swern oxidation / 7.2: Horner-Wadsworth-Emmons olefination / 9.1: Swern oxidation / 10.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/ja0581346