Technology Process of (3E,7E,2R,9R,10R,11S,14R)-1-benzenesulfonyl-9,11,15-tris(tert-butyldimethylsilyloxy)-2,10,14-trimethylpentadeca-3,7-diene
There total 16 articles about (3E,7E,2R,9R,10R,11S,14R)-1-benzenesulfonyl-9,11,15-tris(tert-butyldimethylsilyloxy)-2,10,14-trimethylpentadeca-3,7-diene which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
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856191-06-5
(3E,7E,2R,9R,10R,11S,14R)-9,11,15-tris(tert-butyldimethylsilyloxy)-2,10,14-trimethyl-1-phenylsulfanylpentadeca-3,7-diene
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856190-92-6
(3E,7E,2R,9R,10R,11S,14R)-1-benzenesulfonyl-9,11,15-tris(tert-butyldimethylsilyloxy)-2,10,14-trimethylpentadeca-3,7-diene
- Guidance literature:
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With
diphenyl diselenide; dihydrogen peroxide;
In
diethyl ether;
at -10 - 20 ℃;
for 29h;
DOI:10.1002/anie.200500174
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856190-92-6
(3E,7E,2R,9R,10R,11S,14R)-1-benzenesulfonyl-9,11,15-tris(tert-butyldimethylsilyloxy)-2,10,14-trimethylpentadeca-3,7-diene
- Guidance literature:
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Multi-step reaction with 11 steps
1.1: 86 percent / tetrahydrofuran / 1 h / -15 - 20 °C
2.1: O3 / CH2Cl2 / 0.25 h / -78 °C
2.2: 88 percent / PPh3 / CH2Cl2 / 4.5 h / -78 - 20 °C
3.1: Bu2BOTf; Et3N / CH2Cl2 / 60 h / -80 °C
3.2: 94 percent / phosphate buffer; aq. H2O2 / CH2Cl2; methanol / 6 h / 20 °C / pH 7.2
4.1: 99 percent / imidazole / dimethylformamide / 48 h / 40 °C
5.1: 96 percent / n-BuLi / hexane; tetrahydrofuran / 1.33 h / -78 - -15 °C
6.1: 99 percent / Et3SiH / Pd/C / acetone / 0.5 h / 20 °C
7.1: 49 percent / AgClO4 / Zr(Cp)2(H)(Cl) / CH2Cl2; toluene / 3 h / 0 - 20 °C
8.1: 97 percent / imidazole / dimethylformamide / 20 h
9.1: DDQ / CH2Cl2; H2O / 3.5 h / 0 °C
10.1: 2.14 g / Bu3P; pyridine / 3.5 h / 20 °C
11.1: 91 percent / aq. H2O2; PhSeSePh / diethyl ether / 29 h / -10 - 20 °C
With
pyridine; 1H-imidazole; triethylsilane; n-butyllithium; tributylphosphine; di-n-butylboryl trifluoromethanesulfonate; diphenyl diselenide; dihydrogen peroxide; silver perchlorate; ozone; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
palladium on activated charcoal; Schwartz's reagent;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1002/anie.200500174
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856190-92-6
(3E,7E,2R,9R,10R,11S,14R)-1-benzenesulfonyl-9,11,15-tris(tert-butyldimethylsilyloxy)-2,10,14-trimethylpentadeca-3,7-diene
- Guidance literature:
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Multi-step reaction with 10 steps
1.1: O3 / CH2Cl2 / 0.25 h / -78 °C
1.2: 88 percent / PPh3 / CH2Cl2 / 4.5 h / -78 - 20 °C
2.1: Bu2BOTf; Et3N / CH2Cl2 / 60 h / -80 °C
2.2: 94 percent / phosphate buffer; aq. H2O2 / CH2Cl2; methanol / 6 h / 20 °C / pH 7.2
3.1: 99 percent / imidazole / dimethylformamide / 48 h / 40 °C
4.1: 96 percent / n-BuLi / hexane; tetrahydrofuran / 1.33 h / -78 - -15 °C
5.1: 99 percent / Et3SiH / Pd/C / acetone / 0.5 h / 20 °C
6.1: 49 percent / AgClO4 / Zr(Cp)2(H)(Cl) / CH2Cl2; toluene / 3 h / 0 - 20 °C
7.1: 97 percent / imidazole / dimethylformamide / 20 h
8.1: DDQ / CH2Cl2; H2O / 3.5 h / 0 °C
9.1: 2.14 g / Bu3P; pyridine / 3.5 h / 20 °C
10.1: 91 percent / aq. H2O2; PhSeSePh / diethyl ether / 29 h / -10 - 20 °C
With
pyridine; 1H-imidazole; triethylsilane; n-butyllithium; tributylphosphine; di-n-butylboryl trifluoromethanesulfonate; diphenyl diselenide; dihydrogen peroxide; silver perchlorate; ozone; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
palladium on activated charcoal; Schwartz's reagent;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1002/anie.200500174
