(1S,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-1-[3-(tert-butyl-dimethyl-silanyloxy)-phenylethynyl]-7a-methyl-octahydro-indene

Base Information

• Chemical Name: (1S,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-1-[3-(tert-butyl-dimethyl-silanyloxy)-phenylethynyl]-7a-methyl-octahydro-indene
• CAS No.: 627461-20-5
• Molecular Formula: C₃₀H₅₀O₂Si₂
• Molecular Weight: 498.897
• Mol file: 627461-20-5.mol

Synonyms:(1S,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-1-[3-(tert-butyl-dimethyl-silanyloxy)-phenylethynyl]-7a-methyl-octahydro-indene

Chemical Property of (1S,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-1-[3-(tert-butyl-dimethyl-silanyloxy)-phenylethynyl]-7a-methyl-octahydro-indene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-1-[3-(tert-butyl-dimethyl-silanyloxy)-phenylethynyl]-7a-methyl-octahydro-indene

There total 2 articles about (1S,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-1-[3-(tert-butyl-dimethyl-silanyloxy)-phenylethynyl]-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:

[1S-(1β,4β,7aβ)]-[1R-(3aα)]-octahydro-1-acetyl-4-[(tert-butyldimethylsilyl)oxy]-7a-methyl-1H-indene (140659-43-4) → (1S,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-1-[3-(tert-butyl-dimethyl-silanyloxy)-phenylethynyl]-7a-methyl-octahydro-indene (627461-20-5)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 98 percent / tetrahydrofuran; hexane / 1 h / 20 °C

3: 53 percent / Et₃N / PdCl₂(PPh₃)2 / dimethylformamide / 80 °C

With triethylamine; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; 3: Sonogashira coupling;

DOI:10.1021/ol0351246

Reference yield:

Trifluoro-methanesulfonic acid 1-[(1S,3aR,4S,7aS)-4-(tert-butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-vinyl ester (627461-22-7) → (1S,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-1-[3-(tert-butyl-dimethyl-silanyloxy)-phenylethynyl]-7a-methyl-octahydro-indene (627461-20-5)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With triethylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; 2: Sonogashira coupling;

DOI:10.1021/ol0351246

Reference yield: 70.0%

(1S,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-1-[3-(tert-butyl-dimethyl-silanyloxy)-phenylethynyl]-7a-methyl-octahydro-indene (627461-20-5) → (1S,3aR,7aR)-1-(3-Hydroxy-phenylethynyl)-7a-methyl-octahydro-inden-4-one (627461-26-1)

Guidance literature:

(1S,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-1-[3-(tert-butyl-dimethyl-silanyloxy)-phenylethynyl]-7a-methyl-octahydro-indene; With hydrogen fluoride; at 20 ℃; for 2h;

With dipyridinium dichromate; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1021/ol0351246

upstream raw materials:

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

Trifluoro-methanesulfonic acid 1-[(1S,3aR,4S,7aS)-4-(tert-butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-vinyl ester

Downstream raw materials:

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

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