Technology Process of (3S,4S,6R,10S,12S)-7-Benzenesulfonyl-3,4,12,13-tetrakis-(tert-butyl-dimethyl-silanyloxy)-6,10,14-trimethyl-pentadec-14-ene-2,8-dione
There total 13 articles about (3S,4S,6R,10S,12S)-7-Benzenesulfonyl-3,4,12,13-tetrakis-(tert-butyl-dimethyl-silanyloxy)-6,10,14-trimethyl-pentadec-14-ene-2,8-dione 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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335634-69-0
(4S,6R,10R,12S,13S)-9-Benzenesulfonyl-3,4,12,13-tetrakis-(tert-butyl-dimethyl-silanyloxy)-14,14-diethoxy-2,6,10-trimethyl-pentadec-1-en-8-ol
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443883-68-9
(3S,4S,6R,10S,12S)-7-Benzenesulfonyl-3,4,12,13-tetrakis-(tert-butyl-dimethyl-silanyloxy)-6,10,14-trimethyl-pentadec-14-ene-2,8-dione
- Guidance literature:
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With
oxalyl dichloride; dimethyl sulfoxide; triethylamine;
In
dichloromethane;
at -78 - 0 ℃;
for 3.5h;
DOI:10.1016/S0040-4020(02)00059-5
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443883-68-9
(3S,4S,6R,10S,12S)-7-Benzenesulfonyl-3,4,12,13-tetrakis-(tert-butyl-dimethyl-silanyloxy)-6,10,14-trimethyl-pentadec-14-ene-2,8-dione
- Guidance literature:
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Multi-step reaction with 4 steps
1: dimethylformamide / 12 h
2: 64 percent / p-toluene sulfonic acid / ethanol / 1.5 h / Heating
3: n-BuLi / tetrahydrofuran; petroleum ether / 2.5 h / -78 °C
4: 74 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / 3.5 h / -78 - 0 °C
With
n-butyllithium; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; Petroleum ether;
4: Swern oxidation;
DOI:10.1016/S0040-4020(02)00059-5
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443883-68-9
(3S,4S,6R,10S,12S)-7-Benzenesulfonyl-3,4,12,13-tetrakis-(tert-butyl-dimethyl-silanyloxy)-6,10,14-trimethyl-pentadec-14-ene-2,8-dione
- Guidance literature:
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Multi-step reaction with 6 steps
1: 77 percent / BF3*Et2O / CH2Cl2 / 1.5 h / 0 °C
2: 40 percent / imidazole / dimethylformamide / 24 h / 80 °C
3: 76 percent / SOCl2 / pyridine / 1 h / 0 °C
4: 84 percent / HgCl2; CaCO3 / acetonitrile; H2O / 24 h / Heating
5: n-BuLi / tetrahydrofuran; petroleum ether / 2.5 h / -78 °C
6: 74 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / 3.5 h / -78 - 0 °C
With
1H-imidazole; n-butyllithium; thionyl chloride; oxalyl dichloride; boron trifluoride diethyl etherate; dimethyl sulfoxide; triethylamine; calcium carbonate; mercury dichloride;
In
tetrahydrofuran; pyridine; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; Petroleum ether;
6: Swern oxidation;
DOI:10.1016/S0040-4020(02)00059-5