Technology Process of (2Z,4E,12E,14E)-(6R,7R,8S,9S,10R,16S,17R,18S)-7,9-Bis-(diethyl-isopropyl-silanyloxy)-8-ethyl-17-hydroxy-2,16-dimethoxy-19-[(4-methoxy-phenyl)-diphenyl-methoxy]-4,6,10,12,18-pentamethyl-nonadeca-2,4,12,14-tetraenoic acid methyl ester
There total 25 articles about (2Z,4E,12E,14E)-(6R,7R,8S,9S,10R,16S,17R,18S)-7,9-Bis-(diethyl-isopropyl-silanyloxy)-8-ethyl-17-hydroxy-2,16-dimethoxy-19-[(4-methoxy-phenyl)-diphenyl-methoxy]-4,6,10,12,18-pentamethyl-nonadeca-2,4,12,14-tetraenoic acid methyl ester 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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213408-82-3
(2Z,4E,12E,14E)-(6R,7R,8S,9S,10R,16S,17R,18S)-7,9-Bis-(diethyl-isopropyl-silanyloxy)-8-ethyl-17,19-dihydroxy-2,16-dimethoxy-4,6,10,12,18-pentamethyl-nonadeca-2,4,12,14-tetraenoic acid methyl ester
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213408-83-4
(2Z,4E,12E,14E)-(6R,7R,8S,9S,10R,16S,17R,18S)-7,9-Bis-(diethyl-isopropyl-silanyloxy)-8-ethyl-17-hydroxy-2,16-dimethoxy-19-[(4-methoxy-phenyl)-diphenyl-methoxy]-4,6,10,12,18-pentamethyl-nonadeca-2,4,12,14-tetraenoic acid methyl ester
- Guidance literature:
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With
dmap; triethylamine;
In
dichloromethane;
at 25 ℃;
for 3h;
DOI:10.1021/jo001377q
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213408-83-4
(2Z,4E,12E,14E)-(6R,7R,8S,9S,10R,16S,17R,18S)-7,9-Bis-(diethyl-isopropyl-silanyloxy)-8-ethyl-17-hydroxy-2,16-dimethoxy-19-[(4-methoxy-phenyl)-diphenyl-methoxy]-4,6,10,12,18-pentamethyl-nonadeca-2,4,12,14-tetraenoic acid methyl ester
- Guidance literature:
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Multi-step reaction with 9 steps
1: 72 percent / triphenylarsine; LiCl / tris(dibenzylideneacetone)dipalladium / 1-methyl-pyrrolidin-2-one / 16 h / 40 °C
2: 96 percent / methyllithium / diethyl ether / 0.5 h / 25 °C
3: (COCl)2; DMSO; Et3N / CH2Cl2 / 0.33 h / -78 °C
4: 0.597 g / toluene / 16 h / 100 °C
5: 90 percent / diisobutylaluminum hydride / toluene / 0.5 h / -78 °C
6: 100 percent / MnO2 / CH2Cl2 / 1.5 h / 25 °C
7: 99 percent / potassium bis(trimethylsilyl)amide; 18-crown-6-ether / tetrahydrofuran; toluene / 16 h / -20 °C
8: 96 percent / pyridinium p-toluenesulfonate / methanol / 1 h / 25 °C
9: 100 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 3 h / 25 °C
With
dmap; manganese(IV) oxide; oxalyl dichloride; 18-crown-6 ether; triphenyl-arsane; methyllithium; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium chloride;
tris-(dibenzylideneacetone)dipalladium(0);
In
tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; diethyl ether; dichloromethane; toluene;
1: Stille coupling / 3: Swern oxidation / 4: Wittig reaction / 7: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo001377q
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213408-83-4
(2Z,4E,12E,14E)-(6R,7R,8S,9S,10R,16S,17R,18S)-7,9-Bis-(diethyl-isopropyl-silanyloxy)-8-ethyl-17-hydroxy-2,16-dimethoxy-19-[(4-methoxy-phenyl)-diphenyl-methoxy]-4,6,10,12,18-pentamethyl-nonadeca-2,4,12,14-tetraenoic acid methyl ester
- Guidance literature:
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Multi-step reaction with 12 steps
1.1: 83 percent / pyridine; 4-(dimethylamino)pyridine / CH2Cl2 / 16 h / 25 °C
2.1: 99 percent / 2,6-lutidine / CH2Cl2 / 4 h / 25 °C
3.1: Cp2ZrCl2 / 1,2-dichloro-ethane; hexane / 16 h / 25 °C
3.2: 88 percent / I2 / tetrahydrofuran; 1,2-dichloro-ethane; hexane / 1.5 h / -30 °C
4.1: 72 percent / triphenylarsine; LiCl / tris(dibenzylideneacetone)dipalladium / 1-methyl-pyrrolidin-2-one / 16 h / 40 °C
5.1: 96 percent / methyllithium / diethyl ether / 0.5 h / 25 °C
6.1: (COCl)2; DMSO; Et3N / CH2Cl2 / 0.33 h / -78 °C
7.1: 0.597 g / toluene / 16 h / 100 °C
8.1: 90 percent / diisobutylaluminum hydride / toluene / 0.5 h / -78 °C
9.1: 100 percent / MnO2 / CH2Cl2 / 1.5 h / 25 °C
10.1: 99 percent / potassium bis(trimethylsilyl)amide; 18-crown-6-ether / tetrahydrofuran; toluene / 16 h / -20 °C
11.1: 96 percent / pyridinium p-toluenesulfonate / methanol / 1 h / 25 °C
12.1: 100 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 3 h / 25 °C
With
pyridine; 2,6-dimethylpyridine; dmap; manganese(IV) oxide; oxalyl dichloride; 18-crown-6 ether; triphenyl-arsane; methyllithium; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium chloride;
tris-(dibenzylideneacetone)dipalladium(0); zirconocene dichloride;
In
tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; diethyl ether; hexane; dichloromethane; 1,2-dichloro-ethane; toluene;
4.1: Stille coupling / 6.1: Swern oxidation / 7.1: Wittig reaction / 10.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo001377q
