[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

Base Information

• Chemical Name: [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
• CAS No.: 305796-60-5
• Molecular Formula: C₂₉H₂₈N₂O₁₀S
• Molecular Weight: 596.615

Synonyms:[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

Chemical Property of [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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [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

There total 9 articles about [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 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: 42.0%

dimethyl acetylenedicarboxylate (762-42-5) + (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) → [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 (305796-60-5)

Guidance literature:

With bis(tri-n-butyltin)oxide; In benzene; at 20 ℃; for 2h;

DOI:10.1021/ol006256r

Reference yield:

6,6-dibromopenicillanic acid-1,1-dioxide (76646-91-8) → [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 (305796-60-5)

Guidance literature:

Multi-step reaction with 8 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

8: 42 percent / bis(tributyltin) oxide / benzene / 2 h / 20 °C

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 / 8: Cycloaddition;

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-(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 (305796-60-5)

Guidance literature:

Multi-step reaction with 7 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

7: 42 percent / bis(tributyltin) oxide / benzene / 2 h / 20 °C

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 / 7: Cycloaddition;

DOI:10.1021/ol006256r

upstream raw materials:

dimethyl acetylenedicarboxylate

(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

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

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