p-nitrobenzyl (+/-)-cis-3-<(E)-2-acetamidovinylthio>-6β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

Base Information

• Chemical Name: p-nitrobenzyl (+/-)-cis-3-<(E)-2-acetamidovinylthio>-6β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate
• CAS No.: 74819-56-0
• Molecular Formula: C₂₈H₂₆N₄O₁₁S
• Molecular Weight: 626.601
• Mol file: 74819-56-0.mol

Synonyms:

Chemical Property of p-nitrobenzyl (+/-)-cis-3-<(E)-2-acetamidovinylthio>-6β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-nitrobenzyl (+/-)-cis-3-<(E)-2-acetamidovinylthio>-6β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

There total 10 articles about p-nitrobenzyl (+/-)-cis-3-<(E)-2-acetamidovinylthio>-6β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<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:

magnesium 4-nitrobenzyl malonate (105995-50-4) → p-nitrobenzyl (+/-)-cis-3-<(E)-2-acetamidovinylthio>-6β-<(1S*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (74819-56-0,74843-45-1,77449-49-1,84278-70-6,90694-16-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) N,N'-carbonyldiimidazole

2: p-toluenesulphonyl azide, triethylamine

3: rhodium diacetate

4: 4-dimethylaminopyridine, diisopropylethylamine / acetonitrile

5: NaI / acetonitrile / 0 °C

With rhodium(II) acetate; dmap; 4-toluenesulfonyl azide; triethylamine; N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; sodium iodide; In acetonitrile;

Reference yield:

(+/-)-4β-carboxymethyl-3β-<(1S*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one (76335-76-7,77448-00-1,79299-25-5,90581-13-8,150284-14-3) → p-nitrobenzyl (+/-)-cis-3-<(E)-2-acetamidovinylthio>-6β-<(1S*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (74819-56-0,74843-45-1,77449-49-1,84278-70-6,90694-16-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) N,N'-carbonyldiimidazole

2: p-toluenesulphonyl azide, triethylamine

3: rhodium diacetate

4: 4-dimethylaminopyridine, diisopropylethylamine / acetonitrile

5: NaI / acetonitrile / 0 °C

With rhodium(II) acetate; dmap; 4-toluenesulfonyl azide; triethylamine; N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; sodium iodide; In acetonitrile;

Reference yield:

(+/-)-3β-<(1S*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-4β-(3-p-nitrobenzyloxycarbonyl-2-oxopropyl)azetidin-2-one (76347-45-0,77448-01-2,80559-34-8,80559-36-0,92693-50-0,133443-88-6) → p-nitrobenzyl (+/-)-cis-3-<(E)-2-acetamidovinylthio>-6β-<(1S*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (74819-56-0,74843-45-1,77449-49-1,84278-70-6,90694-16-9)

Guidance literature:

Multi-step reaction with 4 steps

1: p-toluenesulphonyl azide, triethylamine

2: rhodium diacetate

3: 4-dimethylaminopyridine, diisopropylethylamine / acetonitrile

4: NaI / acetonitrile / 0 °C

With rhodium(II) acetate; dmap; 4-toluenesulfonyl azide; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; In acetonitrile;

upstream raw materials:

p-nitrobenzyl (+/-)-cis-6β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-3,7-dioxo-1-azabicyclo<3.2.0>heptane-2-carboxylate

magnesium 4-nitrobenzyl malonate

(+/-)-4β-carboxymethyl-3β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one

(+/-)-4β-formylmethyl-3β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one

Downstream raw materials:

(+/-)-epithienamycin B