(3aR,4S,7S,7aR)-2-Benzoyl-3-benzyl-7-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-5-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one

Base Information

• Chemical Name: (3aR,4S,7S,7aR)-2-Benzoyl-3-benzyl-7-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-5-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one
• CAS No.: 80360-95-8
• Molecular Formula: C₃₄H₄₉NO₃Si₂
• Molecular Weight: 575.939
• Mol file: 80360-95-8.mol

Synonyms:(3aR,4S,7S,7aR)-2-Benzoyl-3-benzyl-7-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-5-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one

Chemical Property of (3aR,4S,7S,7aR)-2-Benzoyl-3-benzyl-7-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-5-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4S,7S,7aR)-2-Benzoyl-3-benzyl-7-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-5-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one

There total 15 articles about (3aR,4S,7S,7aR)-2-Benzoyl-3-benzyl-7-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-5-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-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: 62.0%

1-(tert-butyldimethylsiloxy)-4-<(trimethylsilyl)methyl>-2,4-hexadiene (80360-94-7) + 1-Benzoyl-5-benzyl-1,5-dihydro-pyrrol-2-one (80360-64-1) → (3aR,4R,7R,7aS)-2-Benzoyl-3-benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-7-methyl-6-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one (80360-96-9) + (3aR,4S,7S,7aS)-2-Benzoyl-3-benzyl-7-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-5-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one (80360-99-2) + (3aR,4S,7S,7aR)-2-Benzoyl-3-benzyl-7-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-5-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one (80360-95-8)

Guidance literature:

With 2,6-di-tert-butyl-4-hydroxyphenol; In toluene; at 150 ℃; for 78h;

DOI:10.1021/jo00347a034

Reference yield:

5-benzyl-2,4-pyrrolidinedione (88517-80-0) → (3aR,4S,7S,7aR)-2-Benzoyl-3-benzyl-7-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-5-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one (80360-95-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / sodium cyanoborohydride, chloroacetic acid / methanol / 1 h / Ambient temperature

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

3: triethylamine / tetrahydrofuran; hexane

4: 62 percent / 2,6-di-tert-butylhydroquinone / toluene / 78 h / 150 °C

With n-butyllithium; 2,6-di-tert-butyl-4-hydroxyphenol; sodium cyanoborohydride; triethylamine; chloroacetic acid; In tetrahydrofuran; methanol; hexane; toluene;

DOI:10.1021/jo00347a034

Reference yield:

ethyl 3-(trimethylsilyl)propionate (17728-88-0) → (3aR,4S,7S,7aR)-2-Benzoyl-3-benzyl-7-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-5-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one (80360-95-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) lithium diisopropylamide / 1.) THF, hexane, -78 deg C, 1 h, 2.) -78 deg C, 1.5 h

2: 1.) methanesulfonyl chloride, triethylamine, 2.) DBU / 1.) ether, 0 deg C, 30 min, 2.) THF, 40 deg C, 30 h

3: 91 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 3 h / -78 - 0 °C

4: 86.5 percent / oxalyl chloride, Me₂SO / CH₂Cl₂ / 0.25 h / -78 °C

5: 1.) NaH / 1.) THF, RT, 45 min, 2.) reflux, 1.5 h

6: 87 percent / DIBAL / diethyl ether; hexane / 1.5 h / 0 - 25 °C

7: 84 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

8: 62 percent / 2,6-di-tert-butylhydroquinone / toluene / 78 h / 150 °C

With 1H-imidazole; oxalyl dichloride; 2,6-di-tert-butyl-4-hydroxyphenol; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00347a034

upstream raw materials:

1-(tert-butyldimethylsiloxy)-4-<(trimethylsilyl)methyl>-2,4-hexadiene

1-Benzoyl-5-benzyl-1,5-dihydro-pyrrol-2-one

5-benzyl-2,4-pyrrolidinedione

ethyl 3-(trimethylsilyl)propionate

Downstream raw materials:

(3aR,4S,6R,7S,7aR)-2-Benzoyl-3-benzyl-7-(tert-butyl-dimethyl-silanyloxymethyl)-6-hydroxy-4-methyl-5-methylene-octahydro-isoindol-1-one

(3aR,4S,5R,6S,7S,7aR)-2-Benzoyl-3-benzyl-7-(tert-butyl-dimethyl-silanyloxymethyl)-5,6-dihydroxy-4-methyl-5-trimethylsilanylmethyl-octahydro-isoindol-1-one

(3aR,4S,7S,7aS)-2-Benzoyl-3-benzyl-7-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-5-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one

Acetic acid (3aR,4S,5R,6S,7S,7aR)-6-acetoxy-2-benzoyl-3-benzyl-7-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-1-oxo-5-trimethylsilanylmethyl-octahydro-isoindol-5-yl ester