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

Base Information

• Chemical Name: (6R,7S)-2-(2,2-Dimethyl-propionyl)-7-ethyl-3-methyl-5,5-dioxo-7-phenylselanyl-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-en-8-one
• CAS No.: 204379-11-3
• Molecular Formula: C₂₀H₂₅NO₄SSe
• Molecular Weight: 454.449
• Mol file: 204379-11-3.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R,7S)-2-(2,2-Dimethyl-propionyl)-7-ethyl-3-methyl-5,5-dioxo-7-phenylselanyl-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-en-8-one

There total 6 articles about (6R,7S)-2-(2,2-Dimethyl-propionyl)-7-ethyl-3-methyl-5,5-dioxo-7-phenylselanyl-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:

3-deacetyloxy-7-aminocephalosporanic acid (22252-43-3,26395-99-3,70287-30-8,72059-35-9) → (6R,7S)-2-(2,2-Dimethyl-propionyl)-7-ethyl-3-methyl-5,5-dioxo-7-phenylselanyl-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-en-8-one (204379-11-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 86 percent / Et₃N / dioxane; H₂O / 6 h / Ambient temperature

2: (COCl)2 / tetrahydrofuran / 2 h / 0 - 5 °C

3: CuI, LiCl / tetrahydrofuran / 0.5 h / -70 °C

4: MCPBA / CH₂Cl₂ / 6 h / Ambient temperature

5: 100 percent / TFA / CH₂Cl₂; various solvent(s) / 1 h / Ambient temperature

6: 90 percent / n-BuONO, AcOH / CH₂Cl₂ / 1 h / Heating

7: 1.) THF, -70 deg C, 20 min

With copper(l) iodide; oxalyl dichloride; n-Butyl nitrite; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; lithium chloride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;

DOI:10.1055/s-1998-1621

Reference yield:

(6R,7R)-7-(tert-butyloxycarbonyl)amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-2-carboxylic acid (77359-59-2) → (6R,7S)-2-(2,2-Dimethyl-propionyl)-7-ethyl-3-methyl-5,5-dioxo-7-phenylselanyl-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-en-8-one (204379-11-3)

Guidance literature:

Multi-step reaction with 6 steps

1: (COCl)2 / tetrahydrofuran / 2 h / 0 - 5 °C

2: CuI, LiCl / tetrahydrofuran / 0.5 h / -70 °C

3: MCPBA / CH₂Cl₂ / 6 h / Ambient temperature

4: 100 percent / TFA / CH₂Cl₂; various solvent(s) / 1 h / Ambient temperature

5: 90 percent / n-BuONO, AcOH / CH₂Cl₂ / 1 h / Heating

6: 1.) THF, -70 deg C, 20 min

With copper(l) iodide; oxalyl dichloride; n-Butyl nitrite; acetic acid; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; lithium chloride; In tetrahydrofuran; dichloromethane;

DOI:10.1055/s-1998-1621

Reference yield:

(6R,7R)-7-Amino-2-(2,2-dimethyl-propionyl)-3-methyl-5,5-dioxo-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-en-8-one (174777-87-8) → (6R,7S)-2-(2,2-Dimethyl-propionyl)-7-ethyl-3-methyl-5,5-dioxo-7-phenylselanyl-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-en-8-one (204379-11-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / n-BuONO, AcOH / CH₂Cl₂ / 1 h / Heating

2: 1.) THF, -70 deg C, 20 min

With n-Butyl nitrite; acetic acid; In dichloromethane;

DOI:10.1055/s-1998-1621

upstream raw materials:

Phenylselenyl chloride

triethyl borane

(R)-7-Diazo-2-(2,2-dimethyl-propionyl)-3-methyl-5,5-dioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-en-8-one

3-deacetyloxy-7-aminocephalosporanic acid