(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-((1R,4R)-4-ethyl-1,5-dimethyl-hexyl)-7a-methyl-octahydro-indene

Base Information

• Chemical Name: (1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-((1R,4R)-4-ethyl-1,5-dimethyl-hexyl)-7a-methyl-octahydro-indene
• CAS No.: 1026272-78-5
• Molecular Formula: C₄₁H₇₆O₂Si₂
• Molecular Weight: 657.224

Synonyms:

Chemical Property of (1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-((1R,4R)-4-ethyl-1,5-dimethyl-hexyl)-7a-methyl-octahydro-indene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-((1R,4R)-4-ethyl-1,5-dimethyl-hexyl)-7a-methyl-octahydro-indene

There total 17 articles about (1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-((1R,4R)-4-ethyl-1,5-dimethyl-hexyl)-7a-methyl-octahydro-indene 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:

3,3-Dimethylacryloyl chloride (3350-78-5) → (1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-((1R,4R)-4-ethyl-1,5-dimethyl-hexyl)-7a-methyl-octahydro-indene (1026272-78-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 99 percent / tetrahydrofuran; hexane / 3.5 h / -78 - 0 °C

2.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 1 h / -78 °C

2.2: 55 percent / tetrahydrofuran; toluene / -30 - 0 °C

3.1: 90 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

4.1: 96 percent / H₂ / PtO₂ / ethyl acetate / 2 h / 20 °C

5.1: 95 percent / 4-methylmorpholine N-oxide; tetrapropylammonium perruthenate; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 25 °C

6.1: i-Pr₂NLi / tetrahydrofuran / 1 h / -78 °C

6.2: tetrahydrofuran / 2 h / -78 °C

7.1: 4-(dimethylamino)pyridine; Et₃N / tetrahydrofuran / -78 - 25 °C

8.1: 3 percent sodium amalgam; disodium phosphate / methanol; tetrahydrofuran / -78 - 20 °C

9.1: Bu₄NF / methanol; tetrahydrofuran / 12 h / 25 °C

10.1: 99 percent / H₂ / platinum(IV)oxide hydrate / ethyl acetate / 3 h / 25 °C

11.1: 99 percent / 4-methylmorpholine N-oxide; tetrapropylammonium perruthenate; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.67 h / 25 °C

12.1: n-BuLi / tetrahydrofuran; hexane; pentane / -78 - 25 °C

With dmap; disodium hydrogenphosphate; sodium amalgam; lithium aluminium tetrahydride; n-butyllithium; tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; triethylamine; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate; toluene; pentane; 1.1: Metallation / 1.2: Acylation / 2.1: Metallation / 2.2: Alkylation / 3.1: Reduction / 4.1: Catalytic hydrogenation / 5.1: Oxidation / 6.1: Metallation / 6.2: Addition / 7.1: Acetylation / 8.1: Deacetylation / 9.1: desilylation / 10.1: Catalytic hydrogenation / 11.1: Oxidation / 12.1: Wittig-Horner reaction;

DOI:10.1002/1099-0690(200008)2000:15<2755::AID-EJOC2755>3.0.CO;2-G

Reference yield:

(S)-2-ethyl-3-dimethylbutan-1-ol (56116-35-9) → (1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-((1R,4R)-4-ethyl-1,5-dimethyl-hexyl)-7a-methyl-octahydro-indene (1026272-78-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 95 percent / 4-methylmorpholine N-oxide; tetrapropylammonium perruthenate; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 25 °C

2.1: i-Pr₂NLi / tetrahydrofuran / 1 h / -78 °C

2.2: tetrahydrofuran / 2 h / -78 °C

3.1: 4-(dimethylamino)pyridine; Et₃N / tetrahydrofuran / -78 - 25 °C

4.1: 3 percent sodium amalgam; disodium phosphate / methanol; tetrahydrofuran / -78 - 20 °C

5.1: Bu₄NF / methanol; tetrahydrofuran / 12 h / 25 °C

6.1: 99 percent / H₂ / platinum(IV)oxide hydrate / ethyl acetate / 3 h / 25 °C

7.1: 99 percent / 4-methylmorpholine N-oxide; tetrapropylammonium perruthenate; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.67 h / 25 °C

8.1: n-BuLi / tetrahydrofuran; hexane; pentane / -78 - 25 °C

With dmap; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; 4-methylmorpholine N-oxide; triethylamine; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; pentane; 1.1: Oxidation / 2.1: Metallation / 2.2: Addition / 3.1: Acetylation / 4.1: Deacetylation / 5.1: desilylation / 6.1: Catalytic hydrogenation / 7.1: Oxidation / 8.1: Wittig-Horner reaction;

DOI:10.1002/1099-0690(200008)2000:15<2755::AID-EJOC2755>3.0.CO;2-G

Reference yield:

(S)-2-ethyl-3-methylbutanal (76740-15-3,77790-58-0) → (1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-((1R,4R)-4-ethyl-1,5-dimethyl-hexyl)-7a-methyl-octahydro-indene (1026272-78-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: i-Pr₂NLi / tetrahydrofuran / 1 h / -78 °C

1.2: tetrahydrofuran / 2 h / -78 °C

2.1: 4-(dimethylamino)pyridine; Et₃N / tetrahydrofuran / -78 - 25 °C

3.1: 3 percent sodium amalgam; disodium phosphate / methanol; tetrahydrofuran / -78 - 20 °C

4.1: Bu₄NF / methanol; tetrahydrofuran / 12 h / 25 °C

5.1: 99 percent / H₂ / platinum(IV)oxide hydrate / ethyl acetate / 3 h / 25 °C

6.1: 99 percent / 4-methylmorpholine N-oxide; tetrapropylammonium perruthenate; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.67 h / 25 °C

7.1: n-BuLi / tetrahydrofuran; hexane; pentane / -78 - 25 °C

With dmap; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; 4-methylmorpholine N-oxide; triethylamine; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; pentane; 1.1: Metallation / 1.2: Addition / 2.1: Acetylation / 3.1: Deacetylation / 4.1: desilylation / 5.1: Catalytic hydrogenation / 6.1: Oxidation / 7.1: Wittig-Horner reaction;

DOI:10.1002/1099-0690(200008)2000:15<2755::AID-EJOC2755>3.0.CO;2-G

upstream raw materials:

[(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide

(1R,3aR,7aR)-1-((1R,4R)-4-Ethyl-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-4-one

3,3-Dimethylacryloyl chloride

(S)-2-ethyl-3-dimethylbutan-1-ol

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