Technology Process of (4R,4aR,8aR)-8-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enylethynyl]-4-((R)-1,5-dimethyl-5-triethylsilanyloxy-hexyl)-4a-methyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene
There total 9 articles about (4R,4aR,8aR)-8-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enylethynyl]-4-((R)-1,5-dimethyl-5-triethylsilanyloxy-hexyl)-4a-methyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene which
guide to synthetic route it.
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synthetic route:
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530147-43-4
(4R,4aR,8aR)-8-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enylethynyl]-4-((R)-1,5-dimethyl-5-triethylsilanyloxy-hexyl)-4a-methyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene
- Guidance literature:
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With
copper(l) iodide; diethylamine;
bis(triphenylphosphine) palladium (Il) acetate;
In
acetonitrile;
at 20 ℃;
for 1h;
DOI:10.1039/b209147j
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530147-43-4
(4R,4aR,8aR)-8-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enylethynyl]-4-((R)-1,5-dimethyl-5-triethylsilanyloxy-hexyl)-4a-methyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene
- Guidance literature:
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Multi-step reaction with 10 steps
1.1: 64 percent / DIBAL-H / diethyl ether; hexane; toluene / -78 - 0 °C
2.1: 92 percent / pyridine / 0 °C
3.1: borane-tetrahydrofuran complex / tetrahydrofuran / -20 °C
3.2: NaOH; H2O2 / tetrahydrofuran; H2O / -30 - 20 °C
4.1: 93 percent / sodium iodide / acetone / 60 °C
5.1: pyridine; zinc; NiCl2 / 0.75 h / 65 °C
5.2: 86 percent / pyridine / 1.5 h / 20 °C
6.1: 93 percent / tetrahydrofuran; diethyl ether / 1 h / 20 °C
7.1: pyridinium dichromate / CH2Cl2 / 20 °C
8.1: 88 percent / imidazole / CH2Cl2 / 3 h / 20 °C
9.1: i-Pr2NH; n-BuLi / tetrahydrofuran; hexane / 2.75 h / -78 - 20 °C
9.2: 81 percent / tetrahydrofuran / 4.17 h / -78 - 20 °C
10.1: 91 percent / CuI; Et2NH / Pd(PPh3)2(OAc)2 / acetonitrile / 1 h / 20 °C
With
pyridine; 1H-imidazole; copper(l) iodide; dipyridinium dichromate; n-butyllithium; borane-THF; diisobutylaluminium hydride; diethylamine; diisopropylamine; sodium iodide; nickel dichloride; zinc;
bis(triphenylphosphine) palladium (Il) acetate;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetone; toluene; acetonitrile;
DOI:10.1039/b209147j
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530147-43-4
(4R,4aR,8aR)-8-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enylethynyl]-4-((R)-1,5-dimethyl-5-triethylsilanyloxy-hexyl)-4a-methyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: pyridine; zinc; NiCl2 / 0.75 h / 65 °C
1.2: 86 percent / pyridine / 1.5 h / 20 °C
2.1: 93 percent / tetrahydrofuran; diethyl ether / 1 h / 20 °C
3.1: pyridinium dichromate / CH2Cl2 / 20 °C
4.1: 88 percent / imidazole / CH2Cl2 / 3 h / 20 °C
5.1: i-Pr2NH; n-BuLi / tetrahydrofuran; hexane / 2.75 h / -78 - 20 °C
5.2: 81 percent / tetrahydrofuran / 4.17 h / -78 - 20 °C
6.1: 91 percent / CuI; Et2NH / Pd(PPh3)2(OAc)2 / acetonitrile / 1 h / 20 °C
With
pyridine; 1H-imidazole; copper(l) iodide; dipyridinium dichromate; n-butyllithium; diethylamine; diisopropylamine; nickel dichloride; zinc;
bis(triphenylphosphine) palladium (Il) acetate;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetonitrile;
DOI:10.1039/b209147j