(R)-3-Acetoxymethyl-5,5,8-trioxo-7-vinylidene-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Base Information

• Chemical Name: (R)-3-Acetoxymethyl-5,5,8-trioxo-7-vinylidene-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
• CAS No.: 160032-75-7
• Molecular Formula: C₂₅H₂₁NO₇S
• Molecular Weight: 479.51

Synonyms:(R)-3-Acetoxymethyl-5,5,8-trioxo-7-vinylidene-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Chemical Property of (R)-3-Acetoxymethyl-5,5,8-trioxo-7-vinylidene-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

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Technology Process of (R)-3-Acetoxymethyl-5,5,8-trioxo-7-vinylidene-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

There total 8 articles about (R)-3-Acetoxymethyl-5,5,8-trioxo-7-vinylidene-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl 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: 55.0%

(R)-3-Acetoxymethyl-8-oxo-7-vinylidene-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (160032-72-4) → (R)-3-Acetoxymethyl-5,5,8-trioxo-7-vinylidene-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (160032-75-7)

Guidance literature:

With pH=6.4 phosphate buffer; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; Ambient temperature;

DOI:10.1021/ja00103a010

Reference yield:

benzhydryl 7-oxocephalosporanate (59128-53-9) → (R)-3-Acetoxymethyl-5,5,8-trioxo-7-vinylidene-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (160032-75-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 50 percent / C₂HMgBr / tetrahydrofuran / 2.5 h / -78 - -40 °C

2: 62 percent / pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 98 percent / LiBr, CuBr / tetrahydrofuran / 0.08 h / Ambient temperature

4: 71 percent / Zn-Cu, NH₄Cl / tetrahydrofuran; methanol / 0.5 h / Ambient temperature

5: 55 percent / m-CPBA, buffer (pH=6.4) / CH₂Cl₂ / 0.67 h / Ambient temperature

With pyridine; C₂HMgBr; copper; ammonium chloride; 3-chloro-benzenecarboperoxoic acid; copper(I) bromide; lithium bromide; zinc; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm970351x

Reference yield:

benzhydryl 7-aminocephalosporanate (27266-61-1,54600-89-4) → (R)-3-Acetoxymethyl-5,5,8-trioxo-7-vinylidene-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (160032-75-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) Tf₂O, Et₃N, 2.) aq. HCl / 1.) CH₂Cl₂, from -78 deg C to 0 deg C, 1 h, 2.) CH₂Cl₂, -78 deg C, 30 min

2: 50 percent / C₂HMgBr / tetrahydrofuran / 2.5 h / -78 - -40 °C

3: 62 percent / pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

4: 98 percent / LiBr, CuBr / tetrahydrofuran / 0.08 h / Ambient temperature

5: 71 percent / Zn-Cu, NH₄Cl / tetrahydrofuran; methanol / 0.5 h / Ambient temperature

6: 55 percent / m-CPBA, buffer (pH=6.4) / CH₂Cl₂ / 0.67 h / Ambient temperature

With pyridine; hydrogenchloride; trifluoromethylsulfonic anhydride; C₂HMgBr; copper; ammonium chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; copper(I) bromide; lithium bromide; zinc; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm970351x

upstream raw materials:

(R)-3-Acetoxymethyl-8-oxo-7-vinylidene-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

benzhydryl 7-oxocephalosporanate

benzhydryl 7-aminocephalosporanate

7-Aminocephalosporanic acid

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