4-Nitrobenzyl (1R,5S,6S)-2-{(2S,4S)-2-[4-(2-p'-nitrobenzyloxycarbonyloxyethyl)-1-homopiperazinylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio}-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

Base Information

• Chemical Name: 4-Nitrobenzyl (1R,5S,6S)-2-{(2S,4S)-2-[4-(2-p'-nitrobenzyloxycarbonyloxyethyl)-1-homopiperazinylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio}-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate
• CAS No.: 138508-48-2
• Molecular Formula: C₄₅H₄₉N₇O₁₆S
• Molecular Weight: 975.987

Synonyms:

Chemical Property of 4-Nitrobenzyl (1R,5S,6S)-2-{(2S,4S)-2-[4-(2-p'-nitrobenzyloxycarbonyloxyethyl)-1-homopiperazinylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio}-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of 4-Nitrobenzyl (1R,5S,6S)-2-{(2S,4S)-2-[4-(2-p'-nitrobenzyloxycarbonyloxyethyl)-1-homopiperazinylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio}-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

There total 6 articles about 4-Nitrobenzyl (1R,5S,6S)-2-{(2S,4S)-2-[4-(2-p'-nitrobenzyloxycarbonyloxyethyl)-1-homopiperazinylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio}-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-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:

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) → 4-Nitrobenzyl (1R,5S,6S)-2-{(2S,4S)-2-[4-(2-p'-nitrobenzyloxycarbonyloxyethyl)-1-homopiperazinylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio}-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate (138508-48-2)

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:

carbonic acid 2-[1,4]diazepan-1-yl-ethyl ester 4-nitro-benzyl ester → 4-Nitrobenzyl (1R,5S,6S)-2-{(2S,4S)-2-[4-(2-p'-nitrobenzyloxycarbonyloxyethyl)-1-homopiperazinylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio}-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate (138508-48-2)

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:

(2S,4S)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)-2-pyrrolidinecarboxylic acid (147082-06-2) → 4-Nitrobenzyl (1R,5S,6S)-2-{(2S,4S)-2-[4-(2-p'-nitrobenzyloxycarbonyloxyethyl)-1-homopiperazinylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio}-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate (138508-48-2)

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)-4-Mercapto-2-{4-[2-(4-nitro-benzyloxycarbonyloxy)-ethyl]-[1,4]diazepane-1-carbonyl}-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

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

(2S,4S)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)-2-pyrrolidinecarboxylic acid

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