3-{(1S,3aS,7aS)-7a-Methyl-4-[2-[(3S,5R)-2-methylene-3,5-bis-triisopropylsilanyloxy-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-octahydro-inden-1-ylethynyl}-phenol

Base Information

• Chemical Name: 3-{(1S,3aS,7aS)-7a-Methyl-4-[2-[(3S,5R)-2-methylene-3,5-bis-triisopropylsilanyloxy-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-octahydro-inden-1-ylethynyl}-phenol
• CAS No.: 627461-27-2
• Molecular Formula: C₄₅H₇₂O₃Si₂
• Molecular Weight: 717.236
• Mol file: 627461-27-2.mol

Synonyms:3-{(1S,3aS,7aS)-7a-Methyl-4-[2-[(3S,5R)-2-methylene-3,5-bis-triisopropylsilanyloxy-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-octahydro-inden-1-ylethynyl}-phenol

Chemical Property of 3-{(1S,3aS,7aS)-7a-Methyl-4-[2-[(3S,5R)-2-methylene-3,5-bis-triisopropylsilanyloxy-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-octahydro-inden-1-ylethynyl}-phenol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-{(1S,3aS,7aS)-7a-Methyl-4-[2-[(3S,5R)-2-methylene-3,5-bis-triisopropylsilanyloxy-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-octahydro-inden-1-ylethynyl}-phenol

There total 6 articles about 3-{(1S,3aS,7aS)-7a-Methyl-4-[2-[(3S,5R)-2-methylene-3,5-bis-triisopropylsilanyloxy-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-octahydro-inden-1-ylethynyl}-phenol 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: 75.0%

(1S,3aR,7aR)-1-(3-Hydroxy-phenylethynyl)-7a-methyl-octahydro-inden-4-one (627461-26-1) + C39H63O3PSi2 → 3-{(1S,3aS,7aS)-7a-Methyl-4-[2-[(3S,5R)-2-methylene-3,5-bis-triisopropylsilanyloxy-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-octahydro-inden-1-ylethynyl}-phenol (627461-27-2)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 - -40 ℃;

DOI:10.1021/ol0351246

Reference yield:

1-bromo-3-[(tert-butyldimethylsilyl)oxy]benzene (65423-56-5) → 3-{(1S,3aS,7aS)-7a-Methyl-4-[2-[(3S,5R)-2-methylene-3,5-bis-triisopropylsilanyloxy-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-octahydro-inden-1-ylethynyl}-phenol (627461-27-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 53 percent / Et₃N / PdCl₂(PPh₃)2 / dimethylformamide / 80 °C

2.1: HF / 2 h / 20 °C

2.2: 70 percent / pyridinium dichromate / CH₂Cl₂ / 4 h / 20 °C

3.1: 75 percent / n-BuLi / hexane; tetrahydrofuran / -78 - -40 °C

With n-butyllithium; hydrogen fluoride; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; 1.1: Sonogashira coupling / 3.1: Wittig-Horner coupling;

DOI:10.1021/ol0351246

Reference yield:

[1S-(1β,4β,7aβ)]-[1R-(3aα)]-octahydro-1-acetyl-4-[(tert-butyldimethylsilyl)oxy]-7a-methyl-1H-indene (140659-43-4) → 3-{(1S,3aS,7aS)-7a-Methyl-4-[2-[(3S,5R)-2-methylene-3,5-bis-triisopropylsilanyloxy-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-octahydro-inden-1-ylethynyl}-phenol (627461-27-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 64 percent / LDA / tetrahydrofuran; hexane / 1 h / -78 - 20 °C

2.1: 98 percent / tetrahydrofuran; hexane / 1 h / 20 °C

3.1: 53 percent / Et₃N / PdCl₂(PPh₃)2 / dimethylformamide / 80 °C

4.1: HF / 2 h / 20 °C

4.2: 70 percent / pyridinium dichromate / CH₂Cl₂ / 4 h / 20 °C

5.1: 75 percent / n-BuLi / hexane; tetrahydrofuran / -78 - -40 °C

With n-butyllithium; hydrogen fluoride; triethylamine; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; 3.1: Sonogashira coupling / 5.1: Wittig-Horner coupling;

DOI:10.1021/ol0351246

upstream raw materials:

(1S,3aR,7aR)-1-(3-Hydroxy-phenylethynyl)-7a-methyl-octahydro-inden-4-one

1-bromo-3-[(tert-butyldimethylsilyl)oxy]benzene

[1S-(1β,4β,7aβ)]-[1R-(3aα)]-octahydro-1-acetyl-4-[(tert-butyldimethylsilyl)oxy]-7a-methyl-1H-indene

tert-Butyl-((1R,3aR,4S,7aR)-1-ethynyl-7a-methyl-octahydro-inden-4-yloxy)-dimethyl-silane