(2S,5R,6R)-3,3-Dimethyl-4,4,7-trioxo-6-oxycyanomethyl-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Base Information

• Chemical Name: (2S,5R,6R)-3,3-Dimethyl-4,4,7-trioxo-6-oxycyanomethyl-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester
• CAS No.: 305796-45-6
• Molecular Formula: C₂₃H₂₂N₂O₆S
• Molecular Weight: 454.503

Synonyms:(2S,5R,6R)-3,3-Dimethyl-4,4,7-trioxo-6-oxycyanomethyl-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Chemical Property of (2S,5R,6R)-3,3-Dimethyl-4,4,7-trioxo-6-oxycyanomethyl-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5R,6R)-3,3-Dimethyl-4,4,7-trioxo-6-oxycyanomethyl-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

There total 8 articles about (2S,5R,6R)-3,3-Dimethyl-4,4,7-trioxo-6-oxycyanomethyl-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-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:

(2S,5R,6R)-3,3-dimethyl-4,4,7-trioxo-6-(2-chloro-2-hydroxylimino-ethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester (305796-44-5) → (2S,5R,6R)-3,3-Dimethyl-4,4,7-trioxo-6-oxycyanomethyl-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (305796-45-6)

Guidance literature:

With bis(tri-n-butyltin)oxide; In benzene;

DOI:10.1021/ol006256r

Reference yield:

6,6-dibromopenicillanic acid-1,1-dioxide (76646-91-8) → (2S,5R,6R)-3,3-Dimethyl-4,4,7-trioxo-6-oxycyanomethyl-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (305796-45-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 95 percent / acetone / 2 h / 20 °C

2: 72 percent / AIBN / toluene / 6 h / Heating

3: 75 percent / tributyltin hydride; AIBN / toluene / 3 h / 20 °C

4: 85 percent / ozone; dimethyl sulfide / CH₂Cl₂ / 15 h / 20 °C

5: 90 percent / hydroxylamine hydrochloride; sodium acetate / ethanol; H₂O / 5 h / 20 °C

6: 83 percent / N-chlorosuccinimide / dimethylformamide / 2 h / 20 °C

7: (Bu₃Sn)2O / benzene

With N-chloro-succinimide; dimethylsulfide; 2,2'-azobis(isobutyronitrile); hydroxylamine hydrochloride; tri-n-butyl-tin hydride; sodium acetate; ozone; bis(tri-n-butyltin)oxide; In ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; benzene; 1: Alkylation / 2: Substitution / 3: Substitution / 4: Oxidation / 5: oxime formation / 6: Chlorination / 7: Elimination;

DOI:10.1021/ol006256r

Reference yield:

(2S,5R)-6,6-dibromo-3,3-dimethyl-4,4,7-trioxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester (81324-43-8) → (2S,5R,6R)-3,3-Dimethyl-4,4,7-trioxo-6-oxycyanomethyl-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (305796-45-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 72 percent / AIBN / toluene / 6 h / Heating

2: 75 percent / tributyltin hydride; AIBN / toluene / 3 h / 20 °C

3: 85 percent / ozone; dimethyl sulfide / CH₂Cl₂ / 15 h / 20 °C

4: 90 percent / hydroxylamine hydrochloride; sodium acetate / ethanol; H₂O / 5 h / 20 °C

5: 83 percent / N-chlorosuccinimide / dimethylformamide / 2 h / 20 °C

6: (Bu₃Sn)2O / benzene

With N-chloro-succinimide; dimethylsulfide; 2,2'-azobis(isobutyronitrile); hydroxylamine hydrochloride; tri-n-butyl-tin hydride; sodium acetate; ozone; bis(tri-n-butyltin)oxide; In ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene; 1: Substitution / 2: Substitution / 3: Oxidation / 4: oxime formation / 5: Chlorination / 6: Elimination;

DOI:10.1021/ol006256r

upstream raw materials:

(2S,5R,6R)-3,3-dimethyl-4,4,7-trioxo-6-(2-chloro-2-hydroxylimino-ethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester

6,6-dibromopenicillanic acid-1,1-dioxide

(2S,5R)-6,6-dibromo-3,3-dimethyl-4,4,7-trioxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester

6,6-dibromopenicillanic acid

Downstream raw materials:

[2S,5R,6R]-3,3-dimethyl-4,4,7-trioxo-6-[6-(4-methylphenylsulfonyl)-isoxazol-3-ylmethyl]-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl

[2S,5R,6R]-3,3-dimethyl-4,4,7-trioxo-6-(5-benzoyl-isoxazol-3-ylmethyl)-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl

[2S,5R,6R]-3-(2-benzhydroxycarbonyl-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-azabicyclo[3.2.0]hept-6-ylmethyl)-isoxazole-4,5-dicarboxylic acid dimethyl ester

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