1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[(diphenoxyphosphinyl)oxy]-6-(1-hydroxy-1-methylethyl)-7-oxo-, (4-nitrophenyl)methyl ester, cis-

Base Information

• Chemical Name: 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[(diphenoxyphosphinyl)oxy]-6-(1-hydroxy-1-methylethyl)-7-oxo-, (4-nitrophenyl)methyl ester, cis-
• CAS No.: 90305-08-1
• Molecular Formula: C₂₉H₂₇N₂O₁₀P
• Molecular Weight: 594.515
• Mol file: 90305-08-1.mol

Synonyms:

Chemical Property of 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[(diphenoxyphosphinyl)oxy]-6-(1-hydroxy-1-methylethyl)-7-oxo-, (4-nitrophenyl)methyl ester, cis-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[(diphenoxyphosphinyl)oxy]-6-(1-hydroxy-1-methylethyl)-7-oxo-, (4-nitrophenyl)methyl ester, cis-

There total 4 articles about 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[(diphenoxyphosphinyl)oxy]-6-(1-hydroxy-1-methylethyl)-7-oxo-, (4-nitrophenyl)methyl ester, cis- 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:

p-nitrobenzyl 5,6-cis-6-(1-hydroxy-1-methylethyl)-3,7-dioxo-1-azabicyclo<3.2.0>heptane-2-carboxylate (84787-57-5,86258-46-0,86496-79-9,90580-98-6,92936-43-1,109062-08-0) + chlorophosphoric acid diphenyl ester (2524-64-3) → (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)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 0 ℃; for 1.5h;

Reference yield:

p-nitrobenzyl cis-4-<3-<1-(2-methoxyethoxymethoxy)-1-methylethyl>-4-oxoazetidin-2-yl>-3-oxobutanoate (86191-10-8,87276-65-1) → (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)

Guidance literature:

Multi-step reaction with 4 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

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

Reference yield:

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

Guidance literature:

Multi-step reaction with 3 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

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

upstream raw materials:

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

chlorophosphoric acid diphenyl ester

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

Downstream raw materials:

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

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