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

Base Information

• Chemical Name: 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
• CAS No.: 86489-51-2
• Molecular Formula: C₂₉H₂₈N₄O₁₁S
• Molecular Weight: 640.628
• Mol file: 86489-51-2.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 19 articles about 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 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:

(6R,7R)-7-amino-2,2-dimethyl-3-oxa-1-azabicyclo<4.2.0>octan-8-one (86541-72-2) → 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 (86489-51-2)

Guidance literature:

Multi-step reaction with 9 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 (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 (86489-51-2)

Guidance literature:

Multi-step reaction with 8 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

Reference yield:

(3R,4R)-3-benzyloxycarbonylamino-4-(2-hydroxyethyl)azetidin-2-one (86489-24-9) → 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 (86489-51-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 89 percent / BF₃-Et₂O / CH₂Cl₂

2: H₂ / Pd-C / ethyl acetate

4: n-BuLi / tetrahydrofuran / -78 °C

5: n-Bu₃SnH / AIBN / benzene / Heating

6: 76 percent / n-BuLi / tetrahydrofuran / -78 deg C to 0 deg C

7: 96 percent / AcOH / H₂O / 65 °C

8: 86 percent

With n-butyllithium; boron trifluoride diethyl etherate; hydrogen; tri-n-butyl-tin hydride; acetic acid; palladium on activated charcoal; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; dichloromethane; water; ethyl acetate; benzene;

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

upstream raw materials:

N-((Z)-2-Mercapto-vinyl)-acetamide

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

(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