Technology Process of (5S,7R,9S,12R,13S,14S)-15-((4R,8R,9S,10S,12R,E)-4-acetoxy-10,12-dihydroxy-6,9-dimethylheptadeca-6,16-dien-8-yloxy)-13-(4-methoxybenzyloxy)-2,12,14-trimethyl-15-oxopentadec-1-ene-5,7,9-triyl triacetate
There total 37 articles about (5S,7R,9S,12R,13S,14S)-15-((4R,8R,9S,10S,12R,E)-4-acetoxy-10,12-dihydroxy-6,9-dimethylheptadeca-6,16-dien-8-yloxy)-13-(4-methoxybenzyloxy)-2,12,14-trimethyl-15-oxopentadec-1-ene-5,7,9-triyl triacetate 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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1303438-69-8
(5S,7R,9S,12R,13S,14S)-15-((2S,3R,7R,E)-7-acetoxy-2-((4S,6R)-2,2-dimethyl-6-(pent-4-enyl)-1,3-dioxan-4-yl)-5-methyldec-4-en-3-yloxy)-13-(4-methoxybenzyloxy)-2,12,14-trimethyl-15-oxopentadec-1-ene-5,7,9-triyl triacetate
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1303438-80-3
(5S,7R,9S,12R,13S,14S)-15-((4R,8R,9S,10S,12R,E)-4-acetoxy-10,12-dihydroxy-6,9-dimethylheptadeca-6,16-dien-8-yloxy)-13-(4-methoxybenzyloxy)-2,12,14-trimethyl-15-oxopentadec-1-ene-5,7,9-triyl triacetate
- Guidance literature:
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With
pyridinium p-toluenesulfonate;
In
methanol;
at 20 ℃;
for 4h;
Inert atmosphere;
DOI:10.1021/jo2003506
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1303438-80-3
(5S,7R,9S,12R,13S,14S)-15-((4R,8R,9S,10S,12R,E)-4-acetoxy-10,12-dihydroxy-6,9-dimethylheptadeca-6,16-dien-8-yloxy)-13-(4-methoxybenzyloxy)-2,12,14-trimethyl-15-oxopentadec-1-ene-5,7,9-triyl triacetate
- Guidance literature:
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Multi-step reaction with 12 steps
1.1: sodium tetrahydroborate / ethanol / 0.75 h / 0 - 20 °C / Inert atmosphere
2.1: 1H-imidazole; dmap / dichloromethane / 1.5 h / 20 °C / Inert atmosphere
3.1: palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate / ethyl acetate / 10 h / 20 °C
4.1: 1H-imidazole; triphenylphosphine / tetrahydrofuran / 20 °C / Inert atmosphere
4.2: 0 °C / Inert atmosphere
5.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere
7.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 1 h / -78 °C / Inert atmosphere
8.1: tert.-butyl lithium / diethyl ether; pentane / 0.42 h / -78 - 0 °C / Inert atmosphere
8.2: 1 h / -78 °C / Inert atmosphere
9.1: dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 23.5 h / -78 - -30 °C / Inert atmosphere
10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere
11.1: pyridine; dmap / dichloromethane / 2 h / 20 °C / Inert atmosphere
12.1: pyridinium p-toluenesulfonate / methanol / 4 h / 20 °C / Inert atmosphere
With
pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; oxalyl dichloride; 2,4,6-trichlorobenzoyl chloride; palladium 10% on activated carbon; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate; toluene; pentane;
7.1: Swern oxidation;
DOI:10.1021/jo2003506
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1303438-80-3
(5S,7R,9S,12R,13S,14S)-15-((4R,8R,9S,10S,12R,E)-4-acetoxy-10,12-dihydroxy-6,9-dimethylheptadeca-6,16-dien-8-yloxy)-13-(4-methoxybenzyloxy)-2,12,14-trimethyl-15-oxopentadec-1-ene-5,7,9-triyl triacetate
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: 1H-imidazole; dmap / dichloromethane / 1.5 h / 20 °C / Inert atmosphere
2.1: palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate / ethyl acetate / 10 h / 20 °C
3.1: 1H-imidazole; triphenylphosphine / tetrahydrofuran / 20 °C / Inert atmosphere
3.2: 0 °C / Inert atmosphere
4.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere
6.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 1 h / -78 °C / Inert atmosphere
7.1: tert.-butyl lithium / diethyl ether; pentane / 0.42 h / -78 - 0 °C / Inert atmosphere
7.2: 1 h / -78 °C / Inert atmosphere
8.1: dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 23.5 h / -78 - -30 °C / Inert atmosphere
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere
10.1: pyridine; dmap / dichloromethane / 2 h / 20 °C / Inert atmosphere
11.1: pyridinium p-toluenesulfonate / methanol / 4 h / 20 °C / Inert atmosphere
With
pyridine; 1H-imidazole; dmap; oxalyl dichloride; 2,4,6-trichlorobenzoyl chloride; palladium 10% on activated carbon; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; toluene; pentane;
6.1: Swern oxidation;
DOI:10.1021/jo2003506
