4-nitrobenzyl(5R,6S)-3-(2-acetamido-ethylthio)-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate

Base Information

• Chemical Name: 4-nitrobenzyl(5R,6S)-3-(2-acetamido-ethylthio)-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate
• CAS No.: 86489-46-5
• Molecular Formula: C₂₉H₃₀N₄O₁₁S
• Molecular Weight: 642.643
• Mol file: 86489-46-5.mol

Synonyms:4-nitrobenzyl(5R,6S)-3-(2-acetamido-ethylthio)-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate

Chemical Property of 4-nitrobenzyl(5R,6S)-3-(2-acetamido-ethylthio)-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-nitrobenzyl(5R,6S)-3-(2-acetamido-ethylthio)-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate

There total 10 articles about 4-nitrobenzyl(5R,6S)-3-(2-acetamido-ethylthio)-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-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:

2-(acetylamino)ethanethiol (1190-73-4) + 4-nitrobenzyl (2R,5R,6S)-3,7-dioxo-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-1-azabicyclo[3.2.0]-heptane-2-carboxylate (86489-45-4) + N-ethyl-N,N-diisopropylamine (7087-68-5) + chlorophosphoric acid diphenyl ester (2524-64-3) → 4-nitrobenzyl(5R,6S)-3-(2-acetamido-ethylthio)-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate (86489-46-5)

Guidance literature:

With dmap; In acetonitrile;

Reference yield:

magnesium 4-nitrobenzyl malonate (105995-50-4) → 4-nitrobenzyl(5R,6S)-3-(2-acetamido-ethylthio)-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate (86489-46-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / N,N'-carbonyldiimidazole / tetrahydrofuran / 17 h / Ambient temperature

2: p-TsN₃, Et₃N / acetonitrile / 0.5 h / 0 - 25 °C

3: 95 percent / Rh₂(OAc)4 / diethyl ether / 0.5 h / Heating

4: 1.) (PhO)2POCl, i-Pr₂NEt, DMAP / 1.) CH₃CN, 0 deg C, 1 h; 2.) -15 deg C, 17 h

With dmap; dirhodium tetraacetate; 4-toluenesulfonyl azide; triethylamine; N-ethyl-N,N-diisopropylamine; chlorophosphoric acid diphenyl ester; 1,1'-carbonyldiimidazole; In tetrahydrofuran; diethyl ether; acetonitrile;

DOI:10.1016/S0040-4039(01)91123-2

Reference yield:

2-[(R)-2-Allyl-3-(1-hydroxy-1-methyl-ethyl)-4-oxo-azetidin-1-yl]-3-methyl-but-3-enoic acid methyl ester (96124-69-5) → 4-nitrobenzyl(5R,6S)-3-(2-acetamido-ethylthio)-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate (86489-46-5)

Guidance literature:

Multi-step reaction with 8 steps

1: Et₃N / CH₂Cl₂ / 48 h / Ambient temperature

2: 58.8 percent

3: 61 percent / n-BuLi / tetrahydrofuran / 2.5 h / -78 - 0 °C

4: 64 percent / KMnO₄, NaIO₄ / various solvent(s) / 17 h

5: 78 percent / N,N'-carbonyldiimidazole / tetrahydrofuran / 17 h / Ambient temperature

6: p-TsN₃, Et₃N / acetonitrile / 0.5 h / 0 - 25 °C

7: 95 percent / Rh₂(OAc)4 / diethyl ether / 0.5 h / Heating

8: 1.) (PhO)2POCl, i-Pr₂NEt, DMAP / 1.) CH₃CN, 0 deg C, 1 h; 2.) -15 deg C, 17 h

With dmap; dirhodium tetraacetate; potassium permanganate; sodium periodate; n-butyllithium; 4-toluenesulfonyl azide; triethylamine; N-ethyl-N,N-diisopropylamine; chlorophosphoric acid diphenyl ester; 1,1'-carbonyldiimidazole; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(01)91123-2

upstream raw materials:

2-(acetylamino)ethanethiol

4-nitrobenzyl (2R,5R,6S)-3,7-dioxo-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-1-azabicyclo[3.2.0]-heptane-2-carboxylate

magnesium 4-nitrobenzyl malonate

2-[(R)-2-Allyl-3-(1-hydroxy-1-methyl-ethyl)-4-oxo-azetidin-1-yl]-3-methyl-but-3-enoic acid methyl ester

Downstream raw materials:

4-nitrobenzyl(5R,6S)-3-(2-acetamidoethylsulfinyl)-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-7-oxo-1-azabicyclo[ 3.2.0]-hept-2-ene-2-carboxylate