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

Base Information

• Chemical Name: [2S,5R,6R]-3,3-dimethyl-4,4,7-trioxo-6-(5-methoxycarbonyl-isoxazol-3-ylmethyl)-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester
• CAS No.: 305796-51-4
• Molecular Formula: C₂₇H₂₆N₂O₈S
• Molecular Weight: 538.578

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

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

Chemical Property:

Purity/Quality:

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

There total 8 articles about [2S,5R,6R]-3,3-dimethyl-4,4,7-trioxo-6-(5-methoxycarbonyl-isoxazol-3-ylmethyl)-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl 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:

propynoic acid methyl ester (922-67-8) + (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) → [2S,5R,6R]-3,3-dimethyl-4,4,7-trioxo-6-(5-methoxycarbonyl-isoxazol-3-ylmethyl)-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester (305796-51-4) + [2S,5R,6R]-3,3-dimethyl-4,4,7-trioxo-6-(6-methoxycarbonyl-isoxazol-3-ylmethyl)-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester

Guidance literature:

With bis(tri-n-butyltin)oxide; In benzene; at 20 ℃; for 2h; Title compound not separated from byproducts.;

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-(5-methoxycarbonyl-isoxazol-3-ylmethyl)-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester (305796-51-4)

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: 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]-3,3-dimethyl-4,4,7-trioxo-6-(5-methoxycarbonyl-isoxazol-3-ylmethyl)-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester (305796-51-4)

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: 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:

propynoic acid methyl ester

(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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