(3aS,4R,7R,7aR)-2-Benzoyl-3-benzyl-7-[(E)-4-(tert-butyl-dimethyl-silanyl)-but-1-enyl]-4-methyl-5-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one

Base Information

Chemical Name:(3aS,4R,7R,7aR)-2-Benzoyl-3-benzyl-7-[(E)-4-(tert-butyl-dimethyl-silanyl)-but-1-enyl]-4-methyl-5-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one
CAS No.:80360-98-1
Molecular Formula:C₃₇H₅₃NO₂Si₂
Molecular Weight:600.004
Hs Code.:

(3aS,4R,7R,7aR)-2-Benzoyl-3-benzyl-7-[(E)-4-(tert-butyl-dimethyl-silanyl)-but-1-enyl]-4-methyl-5-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3aS,4R,7R,7aR)-2-Benzoyl-3-benzyl-7-[(E)-4-(tert-butyl-dimethyl-silanyl)-but-1-enyl]-4-methyl-5-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one

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Technology Process of (3aS,4R,7R,7aR)-2-Benzoyl-3-benzyl-7-[(E)-4-(tert-butyl-dimethyl-silanyl)-but-1-enyl]-4-methyl-5-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one

There total 17 articles about (3aS,4R,7R,7aR)-2-Benzoyl-3-benzyl-7-[(E)-4-(tert-butyl-dimethyl-silanyl)-but-1-enyl]-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: 15.0%

: 80360-64-1
1-Benzoyl-5-benzyl-1,5-dihydro-pyrrol-2-one

: 80360-97-0
1-(tert-butyldimethylsiloxy)-6-<(trimethylsilyl)methyl>-2,4,6-octatriene

: 80360-98-1
(3aS,4R,7R,7aR)-2-Benzoyl-3-benzyl-7-[(E)-4-(tert-butyl-dimethyl-silanyl)-but-1-enyl]-4-methyl-5-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one

Guidance literature:: at 150 ℃;
DOI:10.1021/jo00347a034

Reference yield:

: 17728-88-0
ethyl 3-(trimethylsilyl)propionate

: 80360-98-1
(3aS,4R,7R,7aR)-2-Benzoyl-3-benzyl-7-[(E)-4-(tert-butyl-dimethyl-silanyl)-but-1-enyl]-4-methyl-5-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one

Guidance literature:: Multi-step reaction with 11 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: 91 percent / Swern oxidation

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

9: DIBAL

10: imidazole / dimethylformamide / 1.5 h / Ambient temperature

11: 15 percent / 150 °C

With 1H-imidazole; oxalyl dichloride; 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;
DOI:10.1021/jo00347a034

Reference yield:

: 80361-25-7
2-<(trimethylsilyl)methyl>-2-buten-1-ol

: 80360-98-1
(3aS,4R,7R,7aR)-2-Benzoyl-3-benzyl-7-[(E)-4-(tert-butyl-dimethyl-silanyl)-but-1-enyl]-4-methyl-5-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one

Guidance literature:: Multi-step reaction with 8 steps

1: 86.5 percent / oxalyl chloride, Me₂SO / CH₂Cl₂ / 0.25 h / -78 °C

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

3: 87 percent / DIBAL / diethyl ether; hexane / 1.5 h / 0 - 25 °C

4: 91 percent / Swern oxidation

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

6: DIBAL

7: imidazole / dimethylformamide / 1.5 h / Ambient temperature

8: 15 percent / 150 °C

With 1H-imidazole; oxalyl dichloride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; In diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00347a034