4-nitrobenzyl 2-diazo-4-[(2R,3R)-3-{1-methyl-1-(4-nitrobenzyloxycarbonyloxy)-ethyl}-4-oxoazetidin-2-yl]-3-oxobutanoate

Base Information

• Chemical Name: 4-nitrobenzyl 2-diazo-4-[(2R,3R)-3-{1-methyl-1-(4-nitrobenzyloxycarbonyloxy)-ethyl}-4-oxoazetidin-2-yl]-3-oxobutanoate
• CAS No.: 86541-39-1
• Molecular Formula: C₂₅H₂₃N₅O₁₁
• Molecular Weight: 569.485
• Mol file: 86541-39-1.mol

Synonyms:4-nitrobenzyl 2-diazo-4-[(2R,3R)-3-{1-methyl-1-(4-nitrobenzyloxycarbonyloxy)-ethyl}-4-oxoazetidin-2-yl]-3-oxobutanoate

Chemical Property of 4-nitrobenzyl 2-diazo-4-[(2R,3R)-3-{1-methyl-1-(4-nitrobenzyloxycarbonyloxy)-ethyl}-4-oxoazetidin-2-yl]-3-oxobutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-nitrobenzyl 2-diazo-4-[(2R,3R)-3-{1-methyl-1-(4-nitrobenzyloxycarbonyloxy)-ethyl}-4-oxoazetidin-2-yl]-3-oxobutanoate

There total 17 articles about 4-nitrobenzyl 2-diazo-4-[(2R,3R)-3-{1-methyl-1-(4-nitrobenzyloxycarbonyloxy)-ethyl}-4-oxoazetidin-2-yl]-3-oxobutanoate 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:

4-toluenesulfonyl azide (941-55-9) + 4-nitrobenzyl 4-[(2R,3R)-3-{1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl}-4-oxoazetidin-2-yl]-3-oxobutanoate (86541-38-0) → 4-nitrobenzyl 2-diazo-4-[(2R,3R)-3-{1-methyl-1-(4-nitrobenzyloxycarbonyloxy)-ethyl}-4-oxoazetidin-2-yl]-3-oxobutanoate (86541-39-1)

Guidance literature:

With triethylamine; In acetonitrile;

Reference yield:

(6R,7R)-7-amino-2,2-dimethyl-3-oxa-1-azabicyclo<4.2.0>octan-8-one (86541-72-2) → 4-nitrobenzyl 2-diazo-4-[(2R,3R)-3-{1-methyl-1-(4-nitrobenzyloxycarbonyloxy)-ethyl}-4-oxoazetidin-2-yl]-3-oxobutanoate (86541-39-1)

Guidance literature:

Multi-step reaction with 7 steps

2: n-BuLi / tetrahydrofuran / -78 °C

3: n-Bu₃SnH / AIBN / benzene / Heating

4: 76 percent / n-BuLi / tetrahydrofuran / -78 deg C to 0 deg C

5: 96 percent / AcOH / H₂O / 65 °C

6: 86 percent

With n-butyllithium; tri-n-butyl-tin hydride; acetic acid; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; water; benzene;

DOI:10.1016/S0040-4039(00)61885-3

Reference yield:

(6R,7R)-2,2-dimethyl-7-isocyano-1-aza-3-oxabicyclo[4.2.0]octan-8-one (86489-27-2) → 4-nitrobenzyl 2-diazo-4-[(2R,3R)-3-{1-methyl-1-(4-nitrobenzyloxycarbonyloxy)-ethyl}-4-oxoazetidin-2-yl]-3-oxobutanoate (86541-39-1)

Guidance literature:

Multi-step reaction with 6 steps

1: n-BuLi / tetrahydrofuran / -78 °C

2: n-Bu₃SnH / AIBN / benzene / Heating

3: 76 percent / n-BuLi / tetrahydrofuran / -78 deg C to 0 deg C

4: 96 percent / AcOH / H₂O / 65 °C

5: 86 percent

With n-butyllithium; tri-n-butyl-tin hydride; acetic acid; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; water; benzene;

DOI:10.1016/S0040-4039(00)61885-3

upstream raw materials:

{(2R,3R)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-4-oxo-azetidin-2-yl}acetic acid

4-nitrobenzyl chloroformate

(6R,7R)-7-amino-2,2-dimethyl-3-oxa-1-azabicyclo<4.2.0>octan-8-one

(6R,7R)-2,2-dimethyl-7-isocyano-1-aza-3-oxabicyclo[4.2.0]octan-8-one

Downstream raw materials:

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

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

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

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