(S)-5-((R)-2-{(1R,3aS,7aR)-4-[2-[(3S,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-3-methylene-dihydro-furan-2-one

Base Information

• Chemical Name: (S)-5-((R)-2-{(1R,3aS,7aR)-4-[2-[(3S,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-3-methylene-dihydro-furan-2-one
• CAS No.: 590366-82-8
• Molecular Formula: C₄₀H₆₈O₄Si₂
• Molecular Weight: 669.149
• Mol file: 590366-82-8.mol

Synonyms:(S)-5-((R)-2-{(1R,3aS,7aR)-4-[2-[(3S,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-3-methylene-dihydro-furan-2-one

Chemical Property of (S)-5-((R)-2-{(1R,3aS,7aR)-4-[2-[(3S,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-3-methylene-dihydro-furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-5-((R)-2-{(1R,3aS,7aR)-4-[2-[(3S,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-3-methylene-dihydro-furan-2-one

There total 5 articles about (S)-5-((R)-2-{(1R,3aS,7aR)-4-[2-[(3S,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-3-methylene-dihydro-furan-2-one 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:

(3S,4S,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-4-methyloct-1-en-7-yne (203126-90-3) + (S)-5-{(R)-2-[(1R,4E,3aR,7aR)-4-bromomethylene-7a-methylperhydroinden-1-yl]propyl}-3-methylenedihydrofuran-2-one (173388-43-7) → (S)-5-((R)-2-{(1R,3aS,7aR)-4-[2-[(3S,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-3-methylene-dihydro-furan-2-one (590366-82-8)

Guidance literature:

With triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; at 110 ℃; for 2h;

DOI:10.1039/b311107e

Reference yield:

(R)-3-{(1R,3aR,7aR)-4-[1-Bromo-meth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-butyronitrile (173388-40-4) → (S)-5-((R)-2-{(1R,3aS,7aR)-4-[2-[(3S,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-3-methylene-dihydro-furan-2-one (590366-82-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 692 mg / DIBALH / CH₂Cl₂; toluene / 1.5 h / 0 °C

2: 40 percent / aq. NH₄Cl; Zn / tetrahydrofuran / 1.5 h / 0 °C

3: 100 percent / NaH / tetrahydrofuran / 0.5 h / 0 °C

4: Et₃N / Pd(PPh₃)4 / toluene / 2 h / 110 °C

With sodium hydride; diisobutylaluminium hydride; ammonium chloride; triethylamine; zinc; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1039/b311107e

Reference yield:

(1R,4E,3aR,7aR)-4-bromomethylene-1-[(1R)-2-formyl-1-methylethyl]-7a-methylperhydroindene (173388-41-5) → (S)-5-((R)-2-{(1R,3aS,7aR)-4-[2-[(3S,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-3-methylene-dihydro-furan-2-one (590366-82-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 40 percent / aq. NH₄Cl; Zn / tetrahydrofuran / 1.5 h / 0 °C

2: 100 percent / NaH / tetrahydrofuran / 0.5 h / 0 °C

3: Et₃N / Pd(PPh₃)4 / toluene / 2 h / 110 °C

With sodium hydride; ammonium chloride; triethylamine; zinc; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; toluene;

DOI:10.1039/b311107e

upstream raw materials:

(3S,4S,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-4-methyloct-1-en-7-yne

(S)-5-{(R)-2-[(1R,4E,3aR,7aR)-4-bromomethylene-7a-methylperhydroinden-1-yl]propyl}-3-methylenedihydrofuran-2-one

(1R,4E,3aR,7aR)-4-bromomethylene-1-[(1R)-2-formyl-1-methylethyl]-7a-methylperhydroindene

(R)-3-{(1R,3aR,7aR)-4-[1-Bromo-meth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-butyronitrile