(4S,5R,6S)-4-methyl-3-(4-nitro-phenyl)-7-oxo-6-((1'R)-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl-ester

Base Information

• Chemical Name: (4S,5R,6S)-4-methyl-3-(4-nitro-phenyl)-7-oxo-6-((1'R)-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl-ester
• CAS No.: 1354627-13-6
• Molecular Formula: C₂₉H₃₅N₃O₈Si
• Molecular Weight: 581.698
• Mol file: 1354627-13-6.mol

Synonyms:(4S,5R,6S)-4-methyl-3-(4-nitro-phenyl)-7-oxo-6-((1'R)-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl-ester

Chemical Property of (4S,5R,6S)-4-methyl-3-(4-nitro-phenyl)-7-oxo-6-((1'R)-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl-ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R,6S)-4-methyl-3-(4-nitro-phenyl)-7-oxo-6-((1'R)-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl-ester

There total 2 articles about (4S,5R,6S)-4-methyl-3-(4-nitro-phenyl)-7-oxo-6-((1'R)-triethylsilanyloxy-ethyl)-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:

4-nitrophenylboronic acid (24067-17-2) + 4-nitrobenzyl (1R,5R,6S)-1-methyl-6-[(1R)-triethylsilanyloxy-ethyl]-2-(trifluoro-methanesulfonyloxy)-carbapen-2-em-3-carboxylate (165817-82-3) → (4S,5R,6S)-4-methyl-3-(4-nitro-phenyl)-7-oxo-6-((1'R)-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl-ester (1354627-13-6)

Guidance literature:

With potassium hydroxide; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; water; at -78 - 20 ℃; Inert atmosphere;

Reference yield:

(4R,5R,6S)-4-methyl-3,7-dioxo-6-((1'R)-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl-ester (186817-91-4) → (4S,5R,6S)-4-methyl-3-(4-nitro-phenyl)-7-oxo-6-((1'R)-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl-ester (1354627-13-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / dichloromethane / 0.25 h / -78 °C / Inert atmosphere

1.2: 0.5 h / -78 °C / Inert atmosphere

2.1: potassium hydroxide; bis(dibenzylideneacetone)-palladium⁽⁰⁾ / dichloromethane; tetrahydrofuran; water / -78 - 20 °C / Inert atmosphere

With triethylamine; potassium hydroxide; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; water;

Reference yield: 75.0%

(4S,5R,6S)-4-methyl-3-(4-nitro-phenyl)-7-oxo-6-((1'R)-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl-ester (1354627-13-6) → (4S,5R,6S)-6-((1'R)-hydroxyethyl)-4-methyl-3-(4-nitro-phenyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl-ester (1354627-14-7)

Guidance literature:

With hydrogenchloride; water; In tetrahydrofuran; at 20 ℃; for 2h;

upstream raw materials:

4-nitrophenylboronic acid

4-nitrobenzyl (1R,5R,6S)-1-methyl-6-[(1R)-triethylsilanyloxy-ethyl]-2-(trifluoro-methanesulfonyloxy)-carbapen-2-em-3-carboxylate

(4R,5R,6S)-4-methyl-3,7-dioxo-6-((1'R)-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl-ester

Downstream raw materials:

(4S,5R,6S)-6-((1'R)-hydroxyethyl)-4-methyl-3-(4-nitro-phenyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl-ester