p-Nitrobenzyl (5RS,6RS)-6-<(RS)-1-Fluoroethyl>-3-<(2S)-2-p-nitrobenzyloxycarbonyl-2-p-nitrobenzyloxycarbonylamino>ethylthio-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

Base Information

• Chemical Name: p-Nitrobenzyl (5RS,6RS)-6-<(RS)-1-Fluoroethyl>-3-<(2S)-2-p-nitrobenzyloxycarbonyl-2-p-nitrobenzyloxycarbonylamino>ethylthio-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate
• CAS No.: 90497-21-5
• Molecular Formula: C₃₄H₃₀FN₅O₁₃S
• Molecular Weight: 767.702
• Mol file: 90497-21-5.mol

Synonyms:

Chemical Property of p-Nitrobenzyl (5RS,6RS)-6-<(RS)-1-Fluoroethyl>-3-<(2S)-2-p-nitrobenzyloxycarbonyl-2-p-nitrobenzyloxycarbonylamino>ethylthio-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,6RS)-6-<(RS)-1-Fluoroethyl>-3-<(2S)-2-p-nitrobenzyloxycarbonyl-2-p-nitrobenzyloxycarbonylamino>ethylthio-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

There total 3 articles about p-Nitrobenzyl (5RS,6RS)-6-<(RS)-1-Fluoroethyl>-3-<(2S)-2-p-nitrobenzyloxycarbonyl-2-p-nitrobenzyloxycarbonylamino>ethylthio-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:

p-nitrobenzyl 4-<(3RS,4RS)-3-<(RS)-1-fluoroethyl>-2-oxoazetidinin-4-yl>-2-diazo-3-oxobutyrate → p-Nitrobenzyl (5RS,6RS)-6-<(RS)-1-Fluoroethyl>-3-<(2S)-2-p-nitrobenzyloxycarbonyl-2-p-nitrobenzyloxycarbonylamino>ethylthio-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (90497-21-5,96893-61-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / rhodium(II) acetate dimer / benzene / 1 h / 80 °C

2: diisopropylethylamine / dimethylformamide / 0.5 h / -30 °C

3: diisopropylethylamine / dimethylformamide / 0.5 h / -30 °C

With N-ethyl-N,N-diisopropylamine; dirhodium tetraacetate; In N,N-dimethyl-formamide; benzene;

DOI:10.1248/cpb.39.335

Reference yield:

N-p-nitrobenzyloxycarbonyl-D-cysteine p-nitrobenzyl ester (86459-79-2) + 3-(Diphenoxy-phosphoryloxy)-6-(1-fluoro-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (97322-57-1) → p-Nitrobenzyl (5RS,6RS)-6-<(RS)-1-Fluoroethyl>-3-<(2S)-2-p-nitrobenzyloxycarbonyl-2-p-nitrobenzyloxycarbonylamino>ethylthio-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (90497-21-5,96893-61-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at -30 ℃; for 0.5h; Yield given;

DOI:10.1248/cpb.39.335

Reference yield:

p-Nitrobenzyl (5RS,6RS)-3,7-Dioxo-6-<(RS)-1-fluoroethyl>-1-azabicyclo<3.2.0>heptane-2-carboxylate (118713-19-2) → p-Nitrobenzyl (5RS,6RS)-6-<(RS)-1-Fluoroethyl>-3-<(2S)-2-p-nitrobenzyloxycarbonyl-2-p-nitrobenzyloxycarbonylamino>ethylthio-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (90497-21-5,96893-61-7)

Guidance literature:

Multi-step reaction with 2 steps

1: diisopropylethylamine / dimethylformamide / 0.5 h / -30 °C

2: diisopropylethylamine / dimethylformamide / 0.5 h / -30 °C

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;

DOI:10.1248/cpb.39.335

upstream raw materials:

N-p-nitrobenzyloxycarbonyl-D-cysteine p-nitrobenzyl ester

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

p-Nitrobenzyl (5RS,6RS)-3,7-Dioxo-6-<(RS)-1-fluoroethyl>-1-azabicyclo<3.2.0>heptane-2-carboxylate