(6R)-7t-benzoylamino-3-methyl-4,4,7c-tris-methylsulfanyl-5t,8-dioxo-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (6R)-7t-benzoylamino-3-methyl-4,4,7c-tris-methylsulfanyl-5t,8-dioxo-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid methyl ester
• CAS No.: 58482-79-4
• Molecular Formula: C₁₉H₂₂N₂O₅S₄
• Molecular Weight: 486.658

Synonyms:

Chemical Property of (6R)-7t-benzoylamino-3-methyl-4,4,7c-tris-methylsulfanyl-5t,8-dioxo-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R)-7t-benzoylamino-3-methyl-4,4,7c-tris-methylsulfanyl-5t,8-dioxo-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid methyl ester

There total 7 articles about (6R)-7t-benzoylamino-3-methyl-4,4,7c-tris-methylsulfanyl-5t,8-dioxo-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid methyl 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:

3-deacetyloxy-7-aminocephalosporanic acid (22252-43-3,26395-99-3,70287-30-8,72059-35-9) → (6R)-7t-benzoylamino-3-methyl-4,4,7c-tris-methylsulfanyl-5t,8-dioxo-(6rH)-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid methyl ester (58482-79-4)

Guidance literature:

Multi-step reaction with 5 steps

1: (i) Et₃N, aq. THF, (ii) /BRN= 102415/, Et₂O

2: MCPBA / CHCl₃

3: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide

4: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide

5: NaH / hexamethylphosphoric acid triamide

With sodium hydride; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; chloroform;

DOI:10.1248/cpb.23.2507

Reference yield:

(6R)-7t-benzoylamino-3-methyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid methyl ester (58482-84-1) → (6R)-7t-benzoylamino-3-methyl-4,4,7c-tris-methylsulfanyl-5t,8-dioxo-(6rH)-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid methyl ester (58482-79-4)

Guidance literature:

Multi-step reaction with 4 steps

1: MCPBA / CHCl₃

2: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide

3: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide

4: NaH / hexamethylphosphoric acid triamide

With sodium hydride; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; chloroform;

DOI:10.1248/cpb.23.2507

Reference yield:

benzoyl chloride (98-88-4) → (6R)-7t-benzoylamino-3-methyl-4,4,7c-tris-methylsulfanyl-5t,8-dioxo-(6rH)-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid methyl ester (58482-79-4)

Guidance literature:

Multi-step reaction with 5 steps

1: (i) Et₃N, aq. THF, (ii) /BRN= 102415/, Et₂O

2: MCPBA / CHCl₃

3: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide

4: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide

5: NaH / hexamethylphosphoric acid triamide

With sodium hydride; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; chloroform;

DOI:10.1248/cpb.23.2507

upstream raw materials:

methanethiosulfonic acid S-methyl ester

(6R)-7t-benzoylamino-3-methyl-4c,7c-bis-methylsulfanyl-5ξ,8-dioxo-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid methyl ester

3-deacetyloxy-7-aminocephalosporanic acid

(6R)-7t-benzoylamino-3-methyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid methyl ester

Downstream raw materials:

7t-benzoylamino-3-methyl-4,4,7c-tris-methylsulfanyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid methyl ester

3-methylsulfanylthiocarbonyl-2-[(5-oxo-2-phenyl-oxazol-4-ylidenemethyl)-amino]-but-2-enoic acid methyl ester

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