p-Nitrobenzyl (1R,5S,6S)-2-<<(N,N-Bis(p-nitrobenzyloxycarbonyl)pyrazolidin-4-yl>thio>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylate

Base Information

• Chemical Name: p-Nitrobenzyl (1R,5S,6S)-2-<<(N,N-Bis(p-nitrobenzyloxycarbonyl)pyrazolidin-4-yl>thio>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylate
• CAS No.: 120764-68-3
• Molecular Formula: C₃₆H₃₄N₆O₁₄S
• Molecular Weight: 806.764
• Mol file: 120764-68-3.mol

Synonyms:p-Nitrobenzyl (1R,5S,6S)-2-<<(N,N-Bis(p-nitrobenzyloxycarbonyl)pyrazolidin-4-yl>thio>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylate

Chemical Property of p-Nitrobenzyl (1R,5S,6S)-2-<<(N,N-Bis(p-nitrobenzyloxycarbonyl)pyrazolidin-4-yl>thio>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of p-Nitrobenzyl (1R,5S,6S)-2-<<(N,N-Bis(p-nitrobenzyloxycarbonyl)pyrazolidin-4-yl>thio>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylate

There total 2 articles about p-Nitrobenzyl (1R,5S,6S)-2-<<(N,N-Bis(p-nitrobenzyloxycarbonyl)pyrazolidin-4-yl>thio>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-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-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 (93711-81-0,90776-59-3,189188-38-3) + 4-Mercapto-N,N-bis(p-nitro-benzyloxycarbonyl)pyrazolidine (120356-04-9) → p-Nitrobenzyl (1R,5S,6S)-2-<<(N,N-Bis(p-nitrobenzyloxycarbonyl)pyrazolidin-4-yl>thio>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylate (120764-68-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at -5 ℃; for 0.666667h; Yield given;

DOI:10.1021/jo00041a033

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) → p-Nitrobenzyl (1R,5S,6S)-2-<<(N,N-Bis(p-nitrobenzyloxycarbonyl)pyrazolidin-4-yl>thio>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylate (120764-68-3)

Guidance literature:

Multi-step reaction with 2 steps

1: diisopropylethylamine / acetonitrile / 0.5 h / -10 °C

2: diisopropylethylamine / acetonitrile / 0.67 h / -5 °C

With N-ethyl-N,N-diisopropylamine; In acetonitrile;

DOI:10.1021/jo00041a033

Reference yield:

p-Nitrobenzyl (1R,5S,6S)-2-<<(N,N-Bis(p-nitrobenzyloxycarbonyl)pyrazolidin-4-yl>thio>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylate (120764-68-3) → biapenem (120410-24-4)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / 10percent Pd / C / tetrahydrofuran; H₂O / 1.67 h / 3040 Torr / Ambient temperature

2: ethyl formimidate hydrochloride, 1N NaOH / tetrahydrofuran; H₂O / 0.08 h / 0 °C

With sodium hydroxide; ethyl formimidate hydrochloride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; water;

DOI:10.1021/jo00041a033

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

4-Mercapto-N,N-bis(p-nitro-benzyloxycarbonyl)pyrazolidine

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

Downstream raw materials:

biapenem