(6R,9S)-1-aza-3-N-benzoxycarbonylamino-9-methoxycarbonyl-4-phenyl-oxobicyclo[4.3.0]non-3-ene

Base Information

• Chemical Name: (6R,9S)-1-aza-3-N-benzoxycarbonylamino-9-methoxycarbonyl-4-phenyl-oxobicyclo[4.3.0]non-3-ene
• CAS No.: 478239-51-9
• Molecular Formula: C₂₄H₂₄N₂O₅
• Molecular Weight: 420.465
• Mol file: 478239-51-9.mol

Synonyms:(6R,9S)-1-aza-3-N-benzoxycarbonylamino-9-methoxycarbonyl-4-phenyl-oxobicyclo[4.3.0]non-3-ene

Chemical Property of (6R,9S)-1-aza-3-N-benzoxycarbonylamino-9-methoxycarbonyl-4-phenyl-oxobicyclo[4.3.0]non-3-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R,9S)-1-aza-3-N-benzoxycarbonylamino-9-methoxycarbonyl-4-phenyl-oxobicyclo[4.3.0]non-3-ene

There total 7 articles about (6R,9S)-1-aza-3-N-benzoxycarbonylamino-9-methoxycarbonyl-4-phenyl-oxobicyclo[4.3.0]non-3-ene 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:

C25H28N2O6 → (6R,9S)-1-aza-3-N-benzoxycarbonylamino-9-methoxycarbonyl-4-phenyl-oxobicyclo[4.3.0]non-3-ene (478239-51-9)

Guidance literature:

In chloroform; at 20 ℃; for 48h;

DOI:10.1021/ol020160a

Reference yield:

methyl (2S)-cis-(Z)-1-(tert-butyloxycarbonyl)-5-[2'-phenyl-(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-2'-propenyl] prolinate (478239-49-5) → (6R,9S)-1-aza-3-N-benzoxycarbonylamino-9-methoxycarbonyl-4-phenyl-oxobicyclo[4.3.0]non-3-ene (478239-51-9)

Guidance literature:

Multi-step reaction with 2 steps

1: TFA / CH₂Cl₂ / 0.5 h / 20 °C

2: 45 mg / CHCl₃ / 48 h / 20 °C

With trifluoroacetic acid; In dichloromethane; chloroform;

DOI:10.1021/ol020160a

Reference yield:

methyl (2S)-cis-(Z)-1-(tert-butyloxycarbonyl)-5-[2'-bromo-(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-2'-propenyl] prolinate (478239-47-3) → (6R,9S)-1-aza-3-N-benzoxycarbonylamino-9-methoxycarbonyl-4-phenyl-oxobicyclo[4.3.0]non-3-ene (478239-51-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / Pd(OAc)2; P(o-tolyl)3; Na₂CO₃ / 1,2-dimethoxy-ethane; H₂O / 80 °C

2: TFA / CH₂Cl₂ / 0.5 h / 20 °C

3: 45 mg / CHCl₃ / 48 h / 20 °C

With palladium diacetate; sodium carbonate; tris-(o-tolyl)phosphine; trifluoroacetic acid; In 1,2-dimethoxyethane; dichloromethane; chloroform; water; 1: Suzuki cross-coupling;

DOI:10.1021/ol020160a

upstream raw materials:

methyl (2S)-cis-(Z)-1-(tert-butyloxycarbonyl)-5-[2'-bromo-(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-2'-propenyl] prolinate

methyl (2S)-cis-(Z)-1-(tert-butyloxycarbonyl)-5-[2'-phenyl-(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-2'-propenyl] prolinate

(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one

1-(tertbutyloxycarbonyl)-5-(hydroxy)pyrrolidine-2-carboxylic acid methyl ester