p-nitrobenzyl 5,6-cis-3-<(E)-2-acetamidovinylthio>-6-(1-hydroxy-1-methylethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

Base Information

• Chemical Name: p-nitrobenzyl 5,6-cis-3-<(E)-2-acetamidovinylthio>-6-(1-hydroxy-1-methylethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate
• CAS No.: 84273-86-9
• Molecular Formula: C₂₁H₂₃N₃O₇S
• Molecular Weight: 461.496
• Mol file: 84273-86-9.mol

Synonyms:

Chemical Property of p-nitrobenzyl 5,6-cis-3-<(E)-2-acetamidovinylthio>-6-(1-hydroxy-1-methylethyl)-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 5,6-cis-3-<(E)-2-acetamidovinylthio>-6-(1-hydroxy-1-methylethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

There total 5 articles about p-nitrobenzyl 5,6-cis-3-<(E)-2-acetamidovinylthio>-6-(1-hydroxy-1-methylethyl)-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: 67.2%

silver (E)-2-acetamido-1-ethenylthiolate (72618-97-4) + (5R,6R)-3-(Diphenoxy-phosphoryloxy)-6-(1-hydroxy-1-methyl-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (90305-08-1,92531-08-3) → p-nitrobenzyl 5,6-cis-3-<(E)-2-acetamidovinylthio>-6-(1-hydroxy-1-methylethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (84273-86-9,84823-05-2,86258-47-1,89255-28-7,92620-33-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; sodium iodide; In acetonitrile; at 0 ℃; for 2h;

Reference yield:

p-nitrobenzyl cis-4-<3-<1-(2-methoxyethoxymethoxy)-1-methylethyl>-4-oxoazetidin-2-yl>-3-oxobutanoate (86191-10-8,87276-65-1) → p-nitrobenzyl 5,6-cis-3-<(E)-2-acetamidovinylthio>-6-(1-hydroxy-1-methylethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (84273-86-9,84823-05-2,86258-47-1,89255-28-7,92620-33-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 88.3 percent / toluene-p-sulphonyl azide, triethylamine / acetonitrile / 0.5 h / Ambient temperature

2: 81.7 percent / titanium tetrachloride / CH₂Cl₂ / 1 h / 0 °C

3: rhodium(II) diacetate / benzene / 0.75 h / 78 °C

4: di-ispropylethylamine / acetonitrile / 1.5 h / 0 °C

5: 67.2 percent / di-isopropylethylamine, sodium iodide / acetonitrile / 2 h / 0 °C

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

Reference yield:

p-nitrobenzyl cis-2-diazo-4-<3-<1-(2-methoxyethoxymethoxy)-1-methylethyl>-4-oxoazetidin-2-yl>-3-oxobutanoate → p-nitrobenzyl 5,6-cis-3-<(E)-2-acetamidovinylthio>-6-(1-hydroxy-1-methylethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (84273-86-9,84823-05-2,86258-47-1,89255-28-7,92620-33-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 81.7 percent / titanium tetrachloride / CH₂Cl₂ / 1 h / 0 °C

2: rhodium(II) diacetate / benzene / 0.75 h / 78 °C

3: di-ispropylethylamine / acetonitrile / 1.5 h / 0 °C

4: 67.2 percent / di-isopropylethylamine, sodium iodide / acetonitrile / 2 h / 0 °C

With rhodium(II) acetate; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; sodium iodide; In dichloromethane; acetonitrile; benzene;

upstream raw materials:

silver (E)-2-acetamido-1-ethenylthiolate

(5R,6R)-3-(Diphenoxy-phosphoryloxy)-6-(1-hydroxy-1-methyl-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

p-nitrobenzyl cis-4-<3-<1-(2-methoxyethoxymethoxy)-1-methylethyl>-4-oxoazetidin-2-yl>-3-oxobutanoate

p-nitrobenzyl 5,6-cis-6-(1-hydroxy-1-methylethyl)-3,7-dioxo-1-azabicyclo<3.2.0>heptane-2-carboxylate