(4R,4aR,8aR)-8-{(Z)-2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enyl]-vinyl}-4-((R)-1,5-dimethyl-5-triethylsilanyloxy-hexyl)-4a-methyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

Base Information

Chemical Name:(4R,4aR,8aR)-8-{(Z)-2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enyl]-vinyl}-4-((R)-1,5-dimethyl-5-triethylsilanyloxy-hexyl)-4a-methyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene
CAS No.:530147-47-8
Molecular Formula:C₄₆H₈₈O₃Si₃
Molecular Weight:773.459
Hs Code.:

(4R,4aR,8aR)-8-{(Z)-2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enyl]-vinyl}-4-((R)-1,5-dimethyl-5-triethylsilanyloxy-hexyl)-4a-methyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

Synonyms:(4R,4aR,8aR)-8-{(Z)-2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enyl]-vinyl}-4-((R)-1,5-dimethyl-5-triethylsilanyloxy-hexyl)-4a-methyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

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Chemical Property of (4R,4aR,8aR)-8-{(Z)-2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enyl]-vinyl}-4-((R)-1,5-dimethyl-5-triethylsilanyloxy-hexyl)-4a-methyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

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Technology Process of (4R,4aR,8aR)-8-{(Z)-2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enyl]-vinyl}-4-((R)-1,5-dimethyl-5-triethylsilanyloxy-hexyl)-4a-methyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

There total 10 articles about (4R,4aR,8aR)-8-{(Z)-2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enyl]-vinyl}-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. 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:

Reference yield:

: 530147-12-7
(4R,4aR,8aR)-8-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enylethynyl]-4-((R)-1,5-dimethyl-5-triethylsilanyloxy-hexyl)-4a-methyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

: 530147-47-8
(4R,4aR,8aR)-8-{(Z)-2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enyl]-vinyl}-4-((R)-1,5-dimethyl-5-triethylsilanyloxy-hexyl)-4a-methyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

Guidance literature:: With quinoline; hydrogen; Lindlar's catalyst; In ethyl acetate; pentane; at 20 ℃;
DOI:10.1039/b209147j

Reference yield:

: 2-((1R,8aR)-8a-methyl-1,2,3,4,6,7,8,8a-octahydro-1-naphthyl)propionitrile

: 530147-47-8
(4R,4aR,8aR)-8-{(Z)-2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enyl]-vinyl}-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 11 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: 92 percent / CuI; Et₂NH / bis(triphenylphosphine)palladium (II) acetate / acetonitrile / 1 h / 20 °C

11.1: H₂; quinoline / Lindlar catalyst / ethyl acetate; pentane / 20 °C

With pyridine; 1H-imidazole; quinoline; copper(l) iodide; dipyridinium dichromate; n-butyllithium; borane-THF; hydrogen; diisobutylaluminium hydride; diethylamine; diisopropylamine; sodium iodide; nickel dichloride; zinc; Lindlar's catalyst; bis(acetato)bis(triphenylphosphine)palladium⁽⁰⁾; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; acetone; toluene; acetonitrile; pentane;
DOI:10.1039/b209147j

Reference yield:

: 189556-81-8
(6R)-2-methyl-6-((1R,4aR,8aR)-8a-methyl-5-oxodecahydro-1-naphthyl)heptan-2-ol

: 530147-47-8
(4R,4aR,8aR)-8-{(Z)-2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enyl]-vinyl}-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 4 steps

1.1: 88 percent / imidazole / CH₂Cl₂ / 3 h / 20 °C

2.1: i-Pr₂NH; n-BuLi / tetrahydrofuran; hexane / 2.75 h / -78 - 20 °C

2.2: 81 percent / tetrahydrofuran / 4.17 h / -78 - 20 °C

3.1: 92 percent / CuI; Et₂NH / bis(triphenylphosphine)palladium (II) acetate / acetonitrile / 1 h / 20 °C

4.1: H₂; quinoline / Lindlar catalyst / ethyl acetate; pentane / 20 °C

With 1H-imidazole; quinoline; copper(l) iodide; n-butyllithium; hydrogen; diethylamine; diisopropylamine; Lindlar's catalyst; bis(acetato)bis(triphenylphosphine)palladium⁽⁰⁾; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; acetonitrile; pentane;
DOI:10.1039/b209147j