(6R,7S)-2-Benzoyl-7-methoxy-3-methyl-5,5-dioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-en-8-one

Base Information

• Chemical Name: (6R,7S)-2-Benzoyl-7-methoxy-3-methyl-5,5-dioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-en-8-one
• CAS No.: 136933-63-6
• Molecular Formula: C₁₅H₁₅NO₅S
• Molecular Weight: 321.354

Synonyms:(6R,7S)-2-Benzoyl-7-methoxy-3-methyl-5,5-dioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-en-8-one

Chemical Property of (6R,7S)-2-Benzoyl-7-methoxy-3-methyl-5,5-dioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-en-8-one

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Technology Process of (6R,7S)-2-Benzoyl-7-methoxy-3-methyl-5,5-dioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-en-8-one

There total 7 articles about (6R,7S)-2-Benzoyl-7-methoxy-3-methyl-5,5-dioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-en-8-one 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: 90.0%

(6R,7S)-2-Benzoyl-7-methoxy-3-methyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-8-one (204376-70-5) → (6R,7S)-2-Benzoyl-7-methoxy-3-methyl-5,5-dioxo-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-en-8-one (136933-63-6)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In ethyl acetate; for 6h;

DOI:10.1055/s-1998-1620

Reference yield: 85.0%

(6R,7S)-2-Benzoyl-7-methoxy-3-methyl-5,5,8-trioxo-5λ6-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 4-methoxy-benzyl ester (186503-37-7) → (6R,7S)-2-Benzoyl-7-methoxy-3-methyl-5,5-dioxo-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-en-8-one (136933-63-6)

Guidance literature:

With aluminium trichloride; In dichloromethane; at -50 ℃; for 0.75h;

DOI:10.1055/s-1998-1620

Reference yield:

7α-Methoxy-3-methyl-3-cephem-4-carboxylic acid (126621-86-1) → (6R,7S)-2-Benzoyl-7-methoxy-3-methyl-5,5-dioxo-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-en-8-one (136933-63-6)

Guidance literature:

Multi-step reaction with 4 steps

1: NaHCO₃, NaBr / dimethylformamide / 18 h / Ambient temperature

2: 75 percent / LDA / tetrahydrofuran / 1.) -70 deg C, 30 min, 2.) -70 deg C, 90 min

3: 65 percent / AlCl₃ / CH₂Cl₂; various solvent(s) / 0.75 h / -50 °C

4: 90 percent / MCPBA / ethyl acetate / 6 h

With aluminium trichloride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; sodium bromide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1055/s-1998-1620

upstream raw materials:

(6R,7S)-2-Benzoyl-7-methoxy-3-methyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-8-one

(6R,7S)-2-Benzoyl-7-methoxy-3-methyl-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 4-methoxy-benzyl ester

7α-methoxy-3-methyl-Δ³-cephem-4-carbonyl chloride

3-deacetyloxy-7-aminocephalosporanic acid

Downstream raw materials:

2α-bromo-3-(bromomethyl)-7α-methoxy-4-(phenylcarbonyl)-Δ³-cephem 1,1-dioxide

2α-bromo-7α-methoxy-3-methyl-4-(phenylcarbonyl)-Δ³-cephem 1,1-dioxide

3-(bromomethyl)-7α-methoxy-4-(phenylcarbonyl)-Δ³-cephem 1,1-dioxide

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