(4R,5S,6S)-3-[(3S,5S)-5-(4-Carbamoylmethyl-piperazine-1-carbonyl)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Base Information

• Chemical Name: (4R,5S,6S)-3-[(3S,5S)-5-(4-Carbamoylmethyl-piperazine-1-carbonyl)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
• CAS No.: 1053612-94-4
• Molecular Formula: C₃₆H₄₁N₇O₁₂S
• Molecular Weight: 795.827

Synonyms:

Chemical Property of (4R,5S,6S)-3-[(3S,5S)-5-(4-Carbamoylmethyl-piperazine-1-carbonyl)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (4R,5S,6S)-3-[(3S,5S)-5-(4-Carbamoylmethyl-piperazine-1-carbonyl)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

There total 5 articles about (4R,5S,6S)-3-[(3S,5S)-5-(4-Carbamoylmethyl-piperazine-1-carbonyl)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-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:

piperazin-1-yl-acetic acid amide (55829-43-1) → (4R,5S,6S)-3-[(3S,5S)-5-(4-Carbamoylmethyl-piperazine-1-carbonyl)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (1053612-94-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1,1'-carbonyldiimidazole; N,N-diisopropylethylamine / acetonitrile

2: trifluoromethanesulfonic acid; trifluoroacetic acid / methoxybenzene / 1 h / 20 °C

3: N,N-diisopropylethylamine / acetonitrile

With trifluorormethanesulfonic acid; N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; trifluoroacetic acid; In methoxybenzene; acetonitrile; 1: Substitution / 2: Decomposition / 3: Condensation;

DOI:10.7164/antibiotics.51.757

Reference yield:

4-nitrobenzyl (4R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-1-azabicyclo[3.2.0]-heptane-2-carboxylate (104873-15-6) → (4R,5S,6S)-3-[(3S,5S)-5-(4-Carbamoylmethyl-piperazine-1-carbonyl)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (1053612-94-4)

Guidance literature:

Multi-step reaction with 2 steps

1: N,N-diisopropylethylamine / acetonitrile / 1 h / 0 °C

2: N,N-diisopropylethylamine / acetonitrile

With N-ethyl-N,N-diisopropylamine; In acetonitrile; 1: Addition / 2: Condensation;

DOI:10.7164/antibiotics.51.757

Reference yield:

(2S,4S)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)-2-pyrrolidinecarboxylic acid (147082-06-2) → (4R,5S,6S)-3-[(3S,5S)-5-(4-Carbamoylmethyl-piperazine-1-carbonyl)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (1053612-94-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1,1'-carbonyldiimidazole; N,N-diisopropylethylamine / acetonitrile

2: trifluoromethanesulfonic acid; trifluoroacetic acid / methoxybenzene / 1 h / 20 °C

3: N,N-diisopropylethylamine / acetonitrile

With trifluorormethanesulfonic acid; N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; trifluoroacetic acid; In methoxybenzene; acetonitrile; 1: Substitution / 2: Decomposition / 3: Condensation;

DOI:10.7164/antibiotics.51.757

upstream raw materials:

(4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

(2S,4S)-2-(4-Carbamoylmethyl-piperazine-1-carbonyl)-4-mercapto-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

piperazin-1-yl-acetic acid amide

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

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