p-Nitrobenzyl (2RS,3SR,4SR,5SR,6SR)-4-benzoyloxy-3-ethylthio-7-oxo-6-(2-oxoethyl)-1-azabicyclo<3.2.0>heptane-2-carboxylate

Base Information

• Chemical Name: p-Nitrobenzyl (2RS,3SR,4SR,5SR,6SR)-4-benzoyloxy-3-ethylthio-7-oxo-6-(2-oxoethyl)-1-azabicyclo<3.2.0>heptane-2-carboxylate
• CAS No.: 137439-97-5
• Molecular Formula: C₂₅H₂₄N₂O₈S
• Molecular Weight: 512.54
• Mol file: 137439-97-5.mol

Synonyms:p-Nitrobenzyl (2RS,3SR,4SR,5SR,6SR)-4-benzoyloxy-3-ethylthio-7-oxo-6-(2-oxoethyl)-1-azabicyclo<3.2.0>heptane-2-carboxylate

Chemical Property of p-Nitrobenzyl (2RS,3SR,4SR,5SR,6SR)-4-benzoyloxy-3-ethylthio-7-oxo-6-(2-oxoethyl)-1-azabicyclo<3.2.0>heptane-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-Nitrobenzyl (2RS,3SR,4SR,5SR,6SR)-4-benzoyloxy-3-ethylthio-7-oxo-6-(2-oxoethyl)-1-azabicyclo<3.2.0>heptane-2-carboxylate

There total 2 articles about p-Nitrobenzyl (2RS,3SR,4SR,5SR,6SR)-4-benzoyloxy-3-ethylthio-7-oxo-6-(2-oxoethyl)-1-azabicyclo<3.2.0>heptane-2-carboxylate 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: 66.0%

p-Nitrobenzyl (4RS,5SR,6SR)-4-benzoyloxy-7-oxo-6-(2-oxoethyl)-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (112563-67-4) + ethanethiol (75-08-1) → p-Nitrobenzyl (2RS,3SR,4SR,5SR,6SR)-4-benzoyloxy-3-ethylthio-7-oxo-6-(2-oxoethyl)-1-azabicyclo<3.2.0>heptane-2-carboxylate (137439-97-5)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; for 0.0833333h;

DOI:10.1039/P19910002399

Reference yield:

Benzoic acid (1S,5R,6S)-7-[(4-nitro-benzyloxycarbonyl)-(triphenyl-λ5-phosphanylidene)-methyl]-8-oxo-7-aza-bicyclo[4.2.0]oct-3-en-5-yl ester (112563-66-3) → p-Nitrobenzyl (2RS,3SR,4SR,5SR,6SR)-4-benzoyloxy-3-ethylthio-7-oxo-6-(2-oxoethyl)-1-azabicyclo<3.2.0>heptane-2-carboxylate (137439-97-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 29 percent / ozonolysis-cyclisation

2: 66 percent / K₂CO₃ / dimethylformamide / 0.08 h

With potassium carbonate; In N,N-dimethyl-formamide;

DOI:10.1039/P19910002399

Reference yield: 82.0%

p-Nitrobenzyl (2RS,3SR,4SR,5SR,6SR)-4-benzoyloxy-3-ethylthio-7-oxo-6-(2-oxoethyl)-1-azabicyclo<3.2.0>heptane-2-carboxylate (137439-97-5) → p-Nitrobenzyl (2RS,3SR,4SR,5SR,6SR)-4-benzoyloxy-3-ethylthio-6-methyl-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate (137439-98-6)

Guidance literature:

With Wilkinson's catalyst; In dichloromethane; for 16h; Heating;

DOI:10.1039/P19910002399

upstream raw materials:

p-Nitrobenzyl (4RS,5SR,6SR)-4-benzoyloxy-7-oxo-6-(2-oxoethyl)-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

ethanethiol

Benzoic acid (1S,5R,6S)-7-[(4-nitro-benzyloxycarbonyl)-(triphenyl-λ⁵-phosphanylidene)-methyl]-8-oxo-7-aza-bicyclo[4.2.0]oct-3-en-5-yl ester

Downstream raw materials:

p-Nitrobenzyl (2RS,3SR,4SR,5SR,6SR)-4-benzoyloxy-3-ethylthio-6-methyl-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate

p-Nitrobenzyl (4RS,5RS,6RS)-4-benzoyloxy-3-ethylsulphinyl-6-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

p-Nitrobenzyl (4RS,5RS,6RS)-4-benzoyloxy-3-chloro-3-ethylsulphinyl-6-methyl-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate