p-nitrobenzyl (5RS,6SR)-3-acetoxy-6-<(1RS)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

Base Information

• Chemical Name: p-nitrobenzyl (5RS,6SR)-3-acetoxy-6-<(1RS)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate
• CAS No.: 115026-38-5
• Molecular Formula: C₂₆H₂₃N₃O₁₂
• Molecular Weight: 569.482
• Mol file: 115026-38-5.mol

Synonyms:

Chemical Property of p-nitrobenzyl (5RS,6SR)-3-acetoxy-6-<(1RS)-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 (5RS,6SR)-3-acetoxy-6-<(1RS)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

There total 4 articles about p-nitrobenzyl (5RS,6SR)-3-acetoxy-6-<(1RS)-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: 20.0%

p-nitrobenzyl (2RS,5SR,6RS)-3-acetoxy-3-ethylsulphonyl-6-<(1RS)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate (115026-37-4,131613-49-5,131613-50-8) → p-nitrobenzyl (5RS,6SR)-3-acetoxy-6-<(1RS)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (115026-38-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 0.0833333h;

Reference yield:

(5R,6S)-3-Acetoxy-3-ethanesulfonyl-6-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester (115026-37-4,131613-49-5,131613-50-8) → p-nitrobenzyl (5RS,6SR)-3-acetoxy-6-<(1RS)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (115026-38-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4039(00)85383-6

Reference yield:

p-nitrobenzyl (1'RS,5RS,6SR)-6-<1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (87568-67-0,107794-36-5) → p-nitrobenzyl (5RS,6SR)-3-acetoxy-6-<(1RS)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (115026-38-5)

Guidance literature:

Multi-step reaction with 3 steps

2: 2.) m-CPBA / 1.) benzene, reflux, 2 h, 2.) CH₂Cl₂, 0 grad C to room temperature

3: 1,8-diazabicyclo<4.5.0>undec-7-ene (DBU) / CH₂Cl₂ / Ambient temperature

With 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1016/S0040-4039(00)85383-6

upstream raw materials:

p-nitrobenzyl (2RS,5SR,6RS)-3-acetoxy-3-ethylsulphonyl-6-<(1RS)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate

(5R,6S)-3-Acetoxy-3-ethanesulfonyl-6-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

p-nitrobenzyl (1'RS,5RS,6SR)-6-<1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

(5R,6S)-3-Ethylsulfanyl-6-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester