(5R,6R)-3-[2-Amino-2-(4-nitro-benzyloxycarbonyl)-ethylsulfanyl]-6-ethyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Base Information

• Chemical Name: (5R,6R)-3-[2-Amino-2-(4-nitro-benzyloxycarbonyl)-ethylsulfanyl]-6-ethyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
• CAS No.: 81488-15-5
• Molecular Formula: C₂₆H₂₆N₄O₉S
• Molecular Weight: 570.58
• Mol file: 81488-15-5.mol

Synonyms:

Chemical Property of (5R,6R)-3-[2-Amino-2-(4-nitro-benzyloxycarbonyl)-ethylsulfanyl]-6-ethyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,6R)-3-[2-Amino-2-(4-nitro-benzyloxycarbonyl)-ethylsulfanyl]-6-ethyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

There total 2 articles about (5R,6R)-3-[2-Amino-2-(4-nitro-benzyloxycarbonyl)-ethylsulfanyl]-6-ethyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl 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: 67.2%

2-Amino-3-mercapto-propionic acid 4-nitro-benzyl ester (82414-40-2) + PS-5 p-nitrobenzyl ester S-oxide (76217-37-3) → (5R,6R)-3-[2-Amino-2-(4-nitro-benzyloxycarbonyl)-ethylsulfanyl]-6-ethyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (81488-15-5,131613-61-1)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at -35 ℃; for 0.166667h;

DOI:10.1016/S0040-4039(00)86977-4

Reference yield:

p-Nitrobenzyl (5R,6R)-3-(2-acetamidoethylthio)-6-ethyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (71730-34-2) → (5R,6R)-3-[2-Amino-2-(4-nitro-benzyloxycarbonyl)-ethylsulfanyl]-6-ethyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (81488-15-5,131613-61-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0.75 h / -35 °C

2: 67.2 percent / triethylamine / dimethylformamide / 0.17 h / -35 °C

With triethylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)86977-4

upstream raw materials:

2-Amino-3-mercapto-propionic acid 4-nitro-benzyl ester

PS-5 p-nitrobenzyl ester S-oxide

p-Nitrobenzyl (5R,6R)-3-(2-acetamidoethylthio)-6-ethyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate