trimethylsilyl (6R,7R)-7-(4-nitrobenzylidene)amino-3-methylceph-3-em-4-carboxylate

Base Information

• Chemical Name: trimethylsilyl (6R,7R)-7-(4-nitrobenzylidene)amino-3-methylceph-3-em-4-carboxylate
• CAS No.: 95107-17-8
• Molecular Formula: C₁₈H₂₁N₃O₅SSi
• Molecular Weight: 419.533
• Mol file: 95107-17-8.mol

Synonyms:

Chemical Property of trimethylsilyl (6R,7R)-7-(4-nitrobenzylidene)amino-3-methylceph-3-em-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trimethylsilyl (6R,7R)-7-(4-nitrobenzylidene)amino-3-methylceph-3-em-4-carboxylate

There total 1 articles about trimethylsilyl (6R,7R)-7-(4-nitrobenzylidene)amino-3-methylceph-3-em-4-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:

3-deacetyloxy-7-aminocephalosporanic acid (22252-43-3,26395-99-3,70287-30-8,72059-35-9) + 4-nitrobenzaldehdye (555-16-8) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → trimethylsilyl (6R,7R)-7-(4-nitrobenzylidene)amino-3-methylceph-3-em-4-carboxylate (95107-17-8)

Guidance literature:

Yield given. Multistep reaction; 1.) CHCl₃, reflux, 1 h, 2.) CHCl₃, room temperature, 1.5 h;

Reference yield:

trimethylsilyl (6R,7R)-7-(4-nitrobenzylidene)amino-3-methylceph-3-em-4-carboxylate (95107-17-8) → (5'R,6R,7S)-3-methyl-4'-oxo-5'-phenylspiro(1',3'-oxazolidine-2',7-ceph-3-em)-4-carboxylic acid (95107-27-0,95190-66-2)

Guidance literature:

Multi-step reaction with 7 steps

1: LDA / tetrahydrofuran; dimethylformamide / 1.) -75 deg C, 15 min, 2.) -70 deg C, 30 min

2: 99 percent / KHCO₃ / dimethylformamide / Ambient temperature

3: Girard's reagent T, conc.HCl / dimethylformamide; H₂O / 4 h / Ambient temperature

4: propylene oxide / CH₂Cl₂ / Ambient temperature

5: 59 percent / KHCO₃ / methanol; acetone / 1.25 h / Ambient temperature

6: 60 percent / pyridine, mercuric chloride / dimethylformamide / 3 h / Ambient temperature

7: 91 percent / H₂, NaHCO₃ / Pd/C / ethyl acetate; H₂O / 1 h / 20 °C / 2280 Torr

With pyridine; hydrogenchloride; hydrogen; girard's reagent T; sodium hydrogencarbonate; potassium hydrogencarbonate; methyloxirane; mercury dichloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone;

Reference yield:

trimethylsilyl (6R,7R)-7-(4-nitrobenzylidene)amino-3-methylceph-3-em-4-carboxylate (95107-17-8) → 4-nitrobenzyl (5'R,6R,7S)-3-methyl-4'-oxo-5'-phenylspiro(1',3'-oxazolidine-2',7-ceph-3-em)-4-carboxylate (95107-24-7,95190-65-1)

Guidance literature:

Multi-step reaction with 6 steps

1: LDA / tetrahydrofuran; dimethylformamide / 1.) -75 deg C, 15 min, 2.) -70 deg C, 30 min

2: 99 percent / KHCO₃ / dimethylformamide / Ambient temperature

3: Girard's reagent T, conc.HCl / dimethylformamide; H₂O / 4 h / Ambient temperature

4: propylene oxide / CH₂Cl₂ / Ambient temperature

5: 59 percent / KHCO₃ / methanol; acetone / 1.25 h / Ambient temperature

6: 60 percent / pyridine, mercuric chloride / dimethylformamide / 3 h / Ambient temperature

With pyridine; hydrogenchloride; girard's reagent T; potassium hydrogencarbonate; methyloxirane; mercury dichloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

upstream raw materials:

3-deacetyloxy-7-aminocephalosporanic acid

4-nitrobenzaldehdye

1,1,1,3,3,3-hexamethyl-disilazane

Downstream raw materials:

4-nitrobenzyl (6R,7RS)-3',4'-dihydro-3-methyl-4'-oxospiro(2'H-1',3'-benzoxazine-2',7-ceph-3-em)-4-carboxylate

4-nitrobenzyl (2'R,6R,7S)-hydroxy(phenyl)acetylamino-7-methylthio-3-methylceph-3-em-4-carboxylate

4-nitrobenzyl (6R,7S)-7-(2-hydroxybenzoylamino)-3-methyl-7-methylthioceph-3-em-4-carboxylate

4-nitrobenzyl (6R,7S)-3-methyl-7-methylthio-7-(4-nitrobenzylidene)aminoceph-3-em-4-carboxylate

Refernces