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

Base Information

• Chemical Name: 4-nitrobenzyl (1R,5R,6S)-1-methyl-6-[(1R)-triethylsilanyloxy-ethyl]-2-(trifluoro-methanesulfonyloxy)-carbapen-2-em-3-carboxylate
• CAS No.: 165817-82-3
• Molecular Formula: C₂₄H₃₁F₃N₂O₉SSi
• Molecular Weight: 608.665
• Mol file: 165817-82-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about 4-nitrobenzyl (1R,5R,6S)-1-methyl-6-[(1R)-triethylsilanyloxy-ethyl]-2-(trifluoro-methanesulfonyloxy)-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:

trifluoromethylsulfonic anhydride (358-23-6) + (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) → 4-nitrobenzyl (1R,5R,6S)-1-methyl-6-[(1R)-triethylsilanyloxy-ethyl]-2-(trifluoro-methanesulfonyloxy)-carbapen-2-em-3-carboxylate (165817-82-3)

Guidance literature:

With triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -40 ℃; for 1h;

DOI:10.1021/jo980381n

Reference yield:

(γR,2R,3S)-α-diazo-3-[(1R)-1-hydroxyethyl]-γ-methyl-β,4-dioxo-2-azetidinebutanoic acid (4-nitrophenyl)methyl ester (90822-24-5) → 4-nitrobenzyl (1R,5R,6S)-1-methyl-6-[(1R)-triethylsilanyloxy-ethyl]-2-(trifluoro-methanesulfonyloxy)-carbapen-2-em-3-carboxylate (165817-82-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: imidazole / tetrahydrofuran

2.1: ZnCl₂; Rh₂(octa)4 / CH₂Cl₂ / Heating

2.2: Et₃N; i-Pr₂NH / -70 °C

2.3: -70 - -20 °C

With 1H-imidazole; Rh₂(octa)4; zinc(II) chloride; In tetrahydrofuran; dichloromethane; 1.1: silylation / 2.1: Elimination / 2.2: Cyclization / 2.3: sulfonylation;

DOI:10.1021/ol005641d

Reference yield:

trifluoromethylsulfonic anhydride (358-23-6) + (R)-2-Diazo-3-oxo-4-[(2R,3S)-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-2-yl]-pentanoic acid 4-nitro-benzyl ester (186817-88-9) → 4-nitrobenzyl (1R,5R,6S)-1-methyl-6-[(1R)-triethylsilanyloxy-ethyl]-2-(trifluoro-methanesulfonyloxy)-carbapen-2-em-3-carboxylate (165817-82-3)

Guidance literature:

(R)-2-Diazo-3-oxo-4-[(2R,3S)-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-2-yl]-pentanoic acid 4-nitro-benzyl ester; With Rh₂(octa)4; zinc(II) chloride; In dichloromethane; Heating;

With triethylamine; diisopropylamine; at -70 ℃;

trifluoromethylsulfonic anhydride; at -70 - -20 ℃; Further stages.;

DOI:10.1021/ol005641d

upstream raw materials:

trifluoromethylsulfonic anhydride

(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

triethylsilyl trifluoromethyl sulfonate

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

Downstream raw materials:

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

(4S,5R,6S)-4-Methyl-7-oxo-3-(9-oxo-7-trimethylsilanyloxymethyl-9H-fluoren-3-yl)-6-((R)-1-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(4S,5R,6S)-3-(7-Hydroxymethyl-9-oxo-9H-fluoren-3-yl)-4-methyl-7-oxo-6-((R)-1-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(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