(-)-(3aR,4S,7S,7aR,S_S)-4-[(1S)-hydroxypentyl]-7-propyl-2-phenyl-5-(p-tolylsulfinyl)-1,3,3a,4,7,7a-tetrahydro-2H-isoindole-1,3-dione

Base Information

• Chemical Name: (-)-(3aR,4S,7S,7aR,S_S)-4-[(1S)-hydroxypentyl]-7-propyl-2-phenyl-5-(p-tolylsulfinyl)-1,3,3a,4,7,7a-tetrahydro-2H-isoindole-1,3-dione
• CAS No.: 204073-89-2
• Molecular Formula: C₂₉H₃₅NO₄S
• Molecular Weight: 493.667

Synonyms:(-)-(3aR,4S,7S,7aR,S_S)-4-[(1S)-hydroxypentyl]-7-propyl-2-phenyl-5-(p-tolylsulfinyl)-1,3,3a,4,7,7a-tetrahydro-2H-isoindole-1,3-dione

Chemical Property of (-)-(3aR,4S,7S,7aR,S_S)-4-[(1S)-hydroxypentyl]-7-propyl-2-phenyl-5-(p-tolylsulfinyl)-1,3,3a,4,7,7a-tetrahydro-2H-isoindole-1,3-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (-)-(3aR,4S,7S,7aR,S_S)-4-[(1S)-hydroxypentyl]-7-propyl-2-phenyl-5-(p-tolylsulfinyl)-1,3,3a,4,7,7a-tetrahydro-2H-isoindole-1,3-dione

There total 1 articles about (-)-(3aR,4S,7S,7aR,S_S)-4-[(1S)-hydroxypentyl]-7-propyl-2-phenyl-5-(p-tolylsulfinyl)-1,3,3a,4,7,7a-tetrahydro-2H-isoindole-1,3-dione 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: 71.0%

N-phenyl-maleimide (941-69-5) + (-)-(5S,SS)-(6Z,8E)-7-(p-tolylsulfinyl)dodeca-6,8-dien-5-ol (198987-17-6) → (-)-(3aR,4S,7S,7aR,SS)-4-[(1S)-hydroxypentyl]-7-propyl-2-phenyl-5-(p-tolylsulfinyl)-1,3,3a,4,7,7a-tetrahydro-2H-isoindole-1,3-dione (204073-89-2)

Guidance literature:

In toluene; at 20 ℃; for 120h;

DOI:10.1002/chem.200500191

Reference yield: 65.0%

(-)-(3aR,4S,7S,7aR,SS)-4-[(1S)-hydroxypentyl]-7-propyl-2-phenyl-5-(p-tolylsulfinyl)-1,3,3a,4,7,7a-tetrahydro-2H-isoindole-1,3-dione (204073-89-2) → (-)-(3aR,4S,7S,7aR)-4-[(1S)-hydroxypentyl]-2-phenyl-7-propyl-5-(p-tolylsulfonyl)-1,3,3a,4,7,7a-tetrahydro-2H-isoindole-1,3-dione (868565-04-2)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 - 20 ℃; for 2.5h;

DOI:10.1002/chem.200500191

Reference yield:

(-)-(3aR,4S,7S,7aR,SS)-4-[(1S)-hydroxypentyl]-7-propyl-2-phenyl-5-(p-tolylsulfinyl)-1,3,3a,4,7,7a-tetrahydro-2H-isoindole-1,3-dione (204073-89-2) → (-)-(1S,4S,5S,8S,9R)-4-butyl-8-propyl-6-(p-tolylsulfonyl)-3-oxabicyclo[3.3.1]non-6-en-2-one-9-N-phenylcarboxamide

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / mCPBA / CH₂Cl₂ / 2.5 h / -78 - 20 °C

2: 16 mg / SiO₂ / CH₂Cl₂ / 120 h / 20 °C

With silica gel; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1002/chem.200500191

upstream raw materials:

N-phenyl-maleimide

(-)-(5S,S_S)-(6Z,8E)-7-(p-tolylsulfinyl)dodeca-6,8-dien-5-ol

Downstream raw materials:

(-)-(3aR,4S,7S,7aR)-4-[(1S)-hydroxypentyl]-2-phenyl-7-propyl-5-(p-tolylsulfonyl)-1,3,3a,4,7,7a-tetrahydro-2H-isoindole-1,3-dione

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