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

Base Information

• Chemical Name: (5R,6S)-3-(Diphenoxy-phosphoryloxy)-6-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
• CAS No.: 78072-36-3
• Molecular Formula: C₃₆H₃₀N₃O₁₄P
• Molecular Weight: 759.62
• Mol file: 78072-36-3.mol

Synonyms:

Chemical Property of (5R,6S)-3-(Diphenoxy-phosphoryloxy)-6-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,6S)-3-(Diphenoxy-phosphoryloxy)-6-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

There total 16 articles about (5R,6S)-3-(Diphenoxy-phosphoryloxy)-6-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 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 (+/-)-cis-6β-<(1S*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-3,7-dioxo-1-azabicyclo<3.2.0>heptane-2-carboxylate (76335-78-9,77448-03-4,92693-52-2,117407-10-0,133443-89-7) + chlorophosphoric acid diphenyl ester (2524-64-3) → (5R,6R)-3-(Diphenoxy-phosphoryloxy)-6-[(S)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (78072-36-3,96093-91-3,96093-95-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 0 ℃; for 0.166667h;

DOI:10.1039/P19810002282

Reference yield:

(+/-)-p-nitrobenzyl 6α-<(1R*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-3,7-dioxo-1-azabicyclo<3.2.0>heptane-2-carboxylate (76335-78-9,77448-03-4,92693-52-2,117407-10-0,133443-89-7) + chlorophosphoric acid diphenyl ester (2524-64-3) → (5R,6S)-3-(Diphenoxy-phosphoryloxy)-6-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (78072-36-3,96093-91-3,96093-95-7)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 0 ℃; for 1h;

DOI:10.1039/P19810000964

Reference yield:

magnesium 4-nitrobenzyl malonate (105995-50-4) → (5R,6R)-3-(Diphenoxy-phosphoryloxy)-6-[(S)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (78072-36-3,96093-91-3,96093-95-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) N,N'-carbonyldiimidazole

2: p-toluenesulphonyl azide, triethylamine

3: rhodium diacetate

4: 4-dimethylaminopyridine, diisopropylethylamine / acetonitrile

With rhodium(II) acetate; dmap; 4-toluenesulfonyl azide; triethylamine; N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; In acetonitrile;

upstream raw materials:

p-nitrobenzyl (+/-)-cis-6β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-3,7-dioxo-1-azabicyclo<3.2.0>heptane-2-carboxylate

chlorophosphoric acid diphenyl ester

magnesium 4-nitrobenzyl malonate

(+/-)-4β-carboxymethyl-3β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one

Downstream raw materials:

p-nitrobenzyl (+/-)-cis-3-(2-acetamidoethylthio)-6β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

(+/-)-epithienamycin B

(+/-)-epithienamycin A

(+/-)-p-nitrobenzyl 3-<2-(p-nitrobenzyloxycarbonylamino)ethylthio>-6α-<(1R^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate