4-nitrobenzyl (4R,5S,6S)-3-[(2S,4S)-2-(4-carbamoylthiazol-2-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

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Chemical Name:4-nitrobenzyl (4R,5S,6S)-3-[(2S,4S)-2-(4-carbamoylthiazol-2-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
CAS No.:117334-51-7
Molecular Formula:C₃₃H₃₂N₆O₁₁S₂
Molecular Weight:752.783
Hs Code.:

4-nitrobenzyl (4R,5S,6S)-3-[(2S,4S)-2-(4-carbamoylthiazol-2-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

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Chemical Property of 4-nitrobenzyl (4R,5S,6S)-3-[(2S,4S)-2-(4-carbamoylthiazol-2-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

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Technology Process of 4-nitrobenzyl (4R,5S,6S)-3-[(2S,4S)-2-(4-carbamoylthiazol-2-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

There total 7 articles about 4-nitrobenzyl (4R,5S,6S)-3-[(2S,4S)-2-(4-carbamoylthiazol-2-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-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:

: 90822-24-5
(γR,2R,3S)-α-diazo-3-[(1R)-1-hydroxyethyl]-γ-methyl-β,4-dioxo-2-azetidinebutanoic acid (4-nitrophenyl)methyl ester

: 117333-88-7
(2S,4S)-2-(4-carbamoylthiazol-2-yl)-4-mercapto-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

: 117334-51-7
4-nitrobenzyl (4R,5S,6S)-3-[(2S,4S)-2-(4-carbamoylthiazol-2-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Guidance literature:: rhodium(II) acetate;

Reference yield:

: 496048-65-8
(2S,4R)-2-(4-carbamoylthiazol-2-yl)-4-hydroxy-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

: 117334-51-7
4-nitrobenzyl (4R,5S,6S)-3-[(2S,4S)-2-(4-carbamoylthiazol-2-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: Et₃N / CH₂Cl₂ / 0 °C

2: dimethylformamide; toluene / 70 °C

3: aq. NaOH / methanol / cooling

4: N,N-diisopropylethylamine / acetonitrile / 0 °C

With sodium hydroxide; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0223-5234(02)01397-1

Reference yield:

: (2S,4R)-4-Benzoyloxy-2-carbamoyl-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

: 117334-51-7
4-nitrobenzyl (4R,5S,6S)-3-[(2S,4S)-2-(4-carbamoylthiazol-2-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: 94.7 percent / Lawesson's reagent / tetrahydrofuran / 2 h / Heating

2: 89.2 percent / ethanol / 20 h / 20 °C

3: 78.1 percent / aq. NH₄OH / methanol / 20 h / 20 °C

4: Et₃N / CH₂Cl₂ / 0 °C

5: dimethylformamide; toluene / 70 °C

6: aq. NaOH / methanol / cooling

7: N,N-diisopropylethylamine / acetonitrile / 0 °C

With Lawessons reagent; ammonium hydroxide; sodium hydroxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0223-5234(02)01397-1