Technology Process of (2E,4E,10E,12E)-(6R,7S,8S,14S,15R,16S)-17-(tert-Butyl-diphenyl-silanyloxy)-15-(1-ethoxy-ethoxy)-14-methoxy-2,4,6,8,10,16-hexamethyl-7-triethylsilanyloxy-heptadeca-2,4,10,12-tetraenoic acid ethyl ester
There total 24 articles about (2E,4E,10E,12E)-(6R,7S,8S,14S,15R,16S)-17-(tert-Butyl-diphenyl-silanyloxy)-15-(1-ethoxy-ethoxy)-14-methoxy-2,4,6,8,10,16-hexamethyl-7-triethylsilanyloxy-heptadeca-2,4,10,12-tetraenoic acid ethyl ester which
guide to synthetic route it.
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synthetic route:
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186425-19-4
(2E,4E,10E,12E)-(6R,7S,8S,14S,15R,16S)-17-(tert-Butyl-diphenyl-silanyloxy)-15-(1-ethoxy-ethoxy)-14-hydroxy-2,4,6,8,10,16-hexamethyl-7-triethylsilanyloxy-heptadeca-2,4,10,12-tetraenoic acid ethyl ester
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186425-37-6
(2E,4E,10E,12E)-(6R,7S,8S,14S,15R,16S)-17-(tert-Butyl-diphenyl-silanyloxy)-15-(1-ethoxy-ethoxy)-14-methoxy-2,4,6,8,10,16-hexamethyl-7-triethylsilanyloxy-heptadeca-2,4,10,12-tetraenoic acid ethyl ester
- Guidance literature:
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With
potassium hexamethylsilazane;
In
tetrahydrofuran;
at -78 - 0 ℃;
for 6h;
DOI:10.1016/S0040-4039(96)02132-6
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186425-37-6
(2E,4E,10E,12E)-(6R,7S,8S,14S,15R,16S)-17-(tert-Butyl-diphenyl-silanyloxy)-15-(1-ethoxy-ethoxy)-14-methoxy-2,4,6,8,10,16-hexamethyl-7-triethylsilanyloxy-heptadeca-2,4,10,12-tetraenoic acid ethyl ester
- Guidance literature:
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Multi-step reaction with 8 steps
1: imidazole, DMAP / CH2Cl2 / 18 h
2: 88 percent / PPTS / propan-2-ol / 8 h
3: 96 percent / MnO2 / CH2Cl2 / 3 h
4: 87 percent / LiHMDS, ZnCl2 / tetrahydrofuran / 0.75 h / -78 - -50 °C
5: pyridine, DMAP / CH2Cl2 / 4 h / -78 - 0 °C
6: DBU / benzene / 2 h / 10 °C
7: 65 percent / Zn(BH4)2 / diethyl ether / 48 h / -78 - -25 °C
8: 80 percent / KHMDS / tetrahydrofuran / 6 h / -78 - 0 °C
With
pyridine; 1H-imidazole; dmap; manganese(IV) oxide; zinc(II) tetrahydroborate; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride; lithium hexamethyldisilazane;
In
tetrahydrofuran; diethyl ether; dichloromethane; isopropyl alcohol; benzene;
DOI:10.1016/S0040-4039(96)02132-6
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186425-37-6
(2E,4E,10E,12E)-(6R,7S,8S,14S,15R,16S)-17-(tert-Butyl-diphenyl-silanyloxy)-15-(1-ethoxy-ethoxy)-14-methoxy-2,4,6,8,10,16-hexamethyl-7-triethylsilanyloxy-heptadeca-2,4,10,12-tetraenoic acid ethyl ester
- Guidance literature:
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Multi-step reaction with 10 steps
1: 81 percent / tBuOK / tetrahydrofuran / 15 h / -78 - 20 °C
2: 78 percent / TBAF / tetrahydrofuran / 15 h
3: imidazole, DMAP / CH2Cl2 / 18 h
4: 88 percent / PPTS / propan-2-ol / 8 h
5: 96 percent / MnO2 / CH2Cl2 / 3 h
6: 87 percent / LiHMDS, ZnCl2 / tetrahydrofuran / 0.75 h / -78 - -50 °C
7: pyridine, DMAP / CH2Cl2 / 4 h / -78 - 0 °C
8: DBU / benzene / 2 h / 10 °C
9: 65 percent / Zn(BH4)2 / diethyl ether / 48 h / -78 - -25 °C
10: 80 percent / KHMDS / tetrahydrofuran / 6 h / -78 - 0 °C
With
pyridine; 1H-imidazole; dmap; manganese(IV) oxide; zinc(II) tetrahydroborate; potassium tert-butylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride; lithium hexamethyldisilazane;
In
tetrahydrofuran; diethyl ether; dichloromethane; isopropyl alcohol; benzene;
DOI:10.1016/S0040-4039(96)02132-6