p-nitrobenzyl (4R,5S,6S)-3-<(3S,5S)-5-dimethylaminocarbonyl-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio>-4-methyl-7-oxo-6-<(1R)-1-trimethylsilyloxoethyl>-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate

Base Information

• Chemical Name: p-nitrobenzyl (4R,5S,6S)-3-<(3S,5S)-5-dimethylaminocarbonyl-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio>-4-methyl-7-oxo-6-<(1R)-1-trimethylsilyloxoethyl>-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate
• CAS No.: 105344-45-4
• Molecular Formula: C₃₅H₄₃N₅O₁₁SSi
• Molecular Weight: 769.905
• Mol file: 105344-45-4.mol

Synonyms:p-nitrobenzyl (4R,5S,6S)-3-<(3S,5S)-5-dimethylaminocarbonyl-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio>-4-methyl-7-oxo-6-<(1R)-1-trimethylsilyloxoethyl>-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate

Chemical Property of p-nitrobenzyl (4R,5S,6S)-3-<(3S,5S)-5-dimethylaminocarbonyl-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio>-4-methyl-7-oxo-6-<(1R)-1-trimethylsilyloxoethyl>-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-nitrobenzyl (4R,5S,6S)-3-<(3S,5S)-5-dimethylaminocarbonyl-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio>-4-methyl-7-oxo-6-<(1R)-1-trimethylsilyloxoethyl>-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate

There total 12 articles about p-nitrobenzyl (4R,5S,6S)-3-<(3S,5S)-5-dimethylaminocarbonyl-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio>-4-methyl-7-oxo-6-<(1R)-1-trimethylsilyloxoethyl>-1-azabicyclo<3.2.0>hept-2-en-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: 78.0%

bromomagnesium N-isopropyl-N-cyclohexylamide (100207-82-7) + 4-nitrobenzyl (1 R , 5 S , 6 S)-2-(2-diethylcarbamoylphenylsulphinyl)-1-methyl-6-[1(R)-trimethylsilyloxyethyl]-1-carbapen-2-em-3-carboxylate (158168-61-7) + (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine (96034-64-9) → p-nitrobenzyl (4R,5S,6S)-3-<(3S,5S)-5-dimethylaminocarbonyl-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio>-4-methyl-7-oxo-6-<(1R)-1-trimethylsilyloxoethyl>-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate (105344-45-4)

Guidance literature:

With sodium chloride; ammonium chloride; In tetrahydrofuran; (2S)-N-methyl-1-phenylpropan-2-amine hydrate;

Reference yield:

(3S,4S)-4-<(1R)-1-benzyloxycarbonylethyl>-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-2-azetidinone (96035-98-2) → p-nitrobenzyl (4R,5S,6S)-3-<(3S,5S)-5-dimethylaminocarbonyl-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio>-4-methyl-7-oxo-6-<(1R)-1-trimethylsilyloxoethyl>-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate (105344-45-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 100 percent / NaH / tetrahydrofuran / 2 h / 0 °C

2: 100 percent / H₂ / 10percent Pd/C / ethanol / 760 Torr / Ambient temperature

3: Et₃N / CH₂Cl₂ / 1 h

4: CH₂Cl₂ / 1 h

5: 86 percent / anisole, TiCl₄ / CH₂Cl₂ / 1 h / 0 °C

6: 93 percent / γ-collidine / dimethylformamide / 1.5 h / 65 °C

7: 98 percent / Et₃N / toluene / 5 h / Ambient temperature

8: 1.) NaH, 2.) benzyl bromide / 1.) THF, toluene, -20 deg C, 1 h, 2.) THF, toluene, -20 deg C, 2 h

9: DBU / toluene; tetrahydrofuran / 2 h

With 2,4,6-trimethyl-pyridine; hydrogen; benzyl bromide; titanium tetrachloride; sodium hydride; methoxybenzene; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1248/cpb.42.1381

Reference yield:

(2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid (93711-85-4,97101-07-0,113033-46-8,120710-59-0,120710-60-3,90776-58-2) → p-nitrobenzyl (4R,5S,6S)-3-<(3S,5S)-5-dimethylaminocarbonyl-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio>-4-methyl-7-oxo-6-<(1R)-1-trimethylsilyloxoethyl>-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate (105344-45-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 90 percent / K₂CO₃ / acetone / 4 h / Heating

2: 100 percent / NaH / tetrahydrofuran / 2 h / 0 °C

3: 100 percent / H₂ / 10percent Pd/C / ethanol / 760 Torr / Ambient temperature

4: Et₃N / CH₂Cl₂ / 1 h

5: CH₂Cl₂ / 1 h

6: 86 percent / anisole, TiCl₄ / CH₂Cl₂ / 1 h / 0 °C

7: 93 percent / γ-collidine / dimethylformamide / 1.5 h / 65 °C

8: 98 percent / Et₃N / toluene / 5 h / Ambient temperature

9: 1.) NaH, 2.) benzyl bromide / 1.) THF, toluene, -20 deg C, 1 h, 2.) THF, toluene, -20 deg C, 2 h

10: DBU / toluene; tetrahydrofuran / 2 h

With 2,4,6-trimethyl-pyridine; hydrogen; benzyl bromide; titanium tetrachloride; sodium hydride; potassium carbonate; methoxybenzene; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1248/cpb.42.1381

upstream raw materials:

(2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine

(4R,5R,6S,8R)-p-nitrobenzyl-3-(diphenylphosphoryloxy)-4-methyl-6-(1-(trimethylsilyloxy)ethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

(2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid

(3S,4S)-4-<(1R)-1-benzyloxycarbonylethyl>-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-2-azetidinone

Downstream raw materials:

p-nitrobenzyl (4R,5S,6S)-3-<(3S,5S)-5-dimethylaminocarbonyl-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio>-6-<(1R)-1-hydroxyethyl>-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate

Refernces

• 1、 Sunagawa,Sasaki,Matsumura,Goda,Tamoto. "Synthetic studies of carbapenem and penem antibiotics. V. Efficient synthesis of the 1β-methylcarbapenem skeleton". . p. 1381 - 1387. Retrieved 2007/10/02.