4-[(1R,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-cyclohex-3-enecarboxylic acid methyl ester

Base Information

• Chemical Name: 4-[(1R,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-cyclohex-3-enecarboxylic acid methyl ester
• CAS No.: 337528-64-0
• Molecular Formula: C₂₄H₄₂O₃Si
• Molecular Weight: 406.681

Synonyms:4-[(1R,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-cyclohex-3-enecarboxylic acid methyl ester

Chemical Property of 4-[(1R,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-cyclohex-3-enecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[(1R,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-cyclohex-3-enecarboxylic acid methyl ester

There total 7 articles about 4-[(1R,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-cyclohex-3-enecarboxylic acid methyl ester 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:

{(1R,3aR,4S,7aR)-octahydro-1-[(S)-1-iodopropan-2-yl]-7a-methyl-1H-inden-4-yloxy}(tert-butyl)dimethylsilane (100928-05-0) → 4-[(1R,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-cyclohex-3-enecarboxylic acid methyl ester (337528-64-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / potassium t-butoxide / tetrahydrofuran / Heating

2: MCPBA / CH₂Cl₂ / 0 °C

3: magnesium isopropyl-cyclohexylamide / tetrahydrofuran; diethyl ether / 0 - 20 °C

4: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 °C

5: 92 percent / potassium t-butoxide / tetrahydrofuran / 0 °C

6: 97 percent / AlCl₃ / toluene / 25 °C

With aluminium trichloride; magnesium isopropyl-cyclohexylamide; potassium tert-butylate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;

DOI:10.1016/S0039-128X(00)00156-2

Reference yield:

(S)-2-((1R,3aR,4S,7aR)-4-(tert-butyldimethylsilyloxy)-7a-methyloctahydro-1H-inden-1-yl)propan-1-ol (100928-03-8,215509-33-4) → 4-[(1R,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-cyclohex-3-enecarboxylic acid methyl ester (337528-64-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 96 percent / Et₃N / CH₂Cl₂ / 0 °C

2: 97 percent / NaI; K₂CO₃ / acetone / Heating

3: 93 percent / potassium t-butoxide / tetrahydrofuran / Heating

4: MCPBA / CH₂Cl₂ / 0 °C

5: magnesium isopropyl-cyclohexylamide / tetrahydrofuran; diethyl ether / 0 - 20 °C

6: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 °C

7: 92 percent / potassium t-butoxide / tetrahydrofuran / 0 °C

8: 97 percent / AlCl₃ / toluene / 25 °C

With aluminium trichloride; magnesium isopropyl-cyclohexylamide; potassium tert-butylate; potassium carbonate; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; toluene;

DOI:10.1016/S0039-128X(00)00156-2

Reference yield:

[1R-(1β,3aα,7aβ)]-[1S-(4β)]-(1,1-dimethylethyl)dimethyl{[octahydro-7a-methyl-1-(1-methylethenyl)-1H-inden-4-yl]oxy}silane (215257-72-0) → 4-[(1R,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-cyclohex-3-enecarboxylic acid methyl ester (337528-64-0)

Guidance literature:

Multi-step reaction with 5 steps

1: MCPBA / CH₂Cl₂ / 0 °C

2: magnesium isopropyl-cyclohexylamide / tetrahydrofuran; diethyl ether / 0 - 20 °C

3: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 °C

4: 92 percent / potassium t-butoxide / tetrahydrofuran / 0 °C

5: 97 percent / AlCl₃ / toluene / 25 °C

With aluminium trichloride; magnesium isopropyl-cyclohexylamide; potassium tert-butylate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;

DOI:10.1016/S0039-128X(00)00156-2

upstream raw materials:

{(1R,3aR,4S,7aR)-octahydro-1-[(S)-1-iodopropan-2-yl]-7a-methyl-1H-inden-4-yloxy}(tert-butyl)dimethylsilane

(S)-2-((1R,3aR,4S,7aR)-4-(tert-butyldimethylsilyloxy)-7a-methyloctahydro-1H-inden-1-yl)propan-1-ol

[1R-(1β,3aα,7aβ)]-[1S-(4β)]-(1,1-dimethylethyl)dimethyl{[octahydro-7a-methyl-1-(1-methylethenyl)-1H-inden-4-yl]oxy}silane

2-[(1S,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-propenal

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