(2S,3S,5R)-6-[1-tert-Butoxycarbonyl-meth-(Z)-ylidene]-3-((Z)-2-cyano-vinyl)-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Base Information

• Chemical Name: (2S,3S,5R)-6-[1-tert-Butoxycarbonyl-meth-(Z)-ylidene]-3-((Z)-2-cyano-vinyl)-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester
• CAS No.: 229616-97-1
• Molecular Formula: C₂₉H₂₈N₂O₇S
• Molecular Weight: 548.617

Synonyms:

Chemical Property of (2S,3S,5R)-6-[1-tert-Butoxycarbonyl-meth-(Z)-ylidene]-3-((Z)-2-cyano-vinyl)-3-methyl-4,4,7-trioxo-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,3S,5R)-6-[1-tert-Butoxycarbonyl-meth-(Z)-ylidene]-3-((Z)-2-cyano-vinyl)-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

There total 8 articles about (2S,3S,5R)-6-[1-tert-Butoxycarbonyl-meth-(Z)-ylidene]-3-((Z)-2-cyano-vinyl)-3-methyl-4,4,7-trioxo-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:

benzhydryl 6-oxopenicillinate (129792-01-4) → (2S,3S,5R)-6-[1-tert-Butoxycarbonyl-meth-(Z)-ylidene]-3-((Z)-2-cyano-vinyl)-3-methyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (229616-97-1)

Guidance literature:

Multi-step reaction with 8 steps

1: -78 °C

2: MCPBA / CH₂Cl₂

3: toluene / Heating

4: AgOAc / CH₂Cl₂

5: (H₂N)2C=S, pyridine / dimethylformamide

6: Cl(CO)2Cl, DMSO

7: LiClO₄ / acetonitrile

8: MCPBA

With pyridine; oxalyl dichloride; silver(I) acetate; lithium perchlorate; dimethyl sulfoxide; thiourea; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0960-894X(99)00325-X

Reference yield:

benzhydryl 6-(Z)-(1-tert-butoxycarbonylmethylene)penicillanate (167028-46-8) → (2S,3S,5R)-6-[1-tert-Butoxycarbonyl-meth-(Z)-ylidene]-3-((Z)-2-cyano-vinyl)-3-methyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (229616-97-1)

Guidance literature:

Multi-step reaction with 7 steps

1: MCPBA / CH₂Cl₂

2: toluene / Heating

3: AgOAc / CH₂Cl₂

4: (H₂N)2C=S, pyridine / dimethylformamide

5: Cl(CO)2Cl, DMSO

6: LiClO₄ / acetonitrile

7: MCPBA

With pyridine; oxalyl dichloride; silver(I) acetate; lithium perchlorate; dimethyl sulfoxide; thiourea; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0960-894X(99)00325-X

Reference yield:

(2S,4R,5R)-6-[1-tert-Butoxycarbonyl-meth-(Z)-ylidene]-3,3-dimethyl-4,7-dioxo-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (247115-05-5) → (2S,3S,5R)-6-[1-tert-Butoxycarbonyl-meth-(Z)-ylidene]-3-((Z)-2-cyano-vinyl)-3-methyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (229616-97-1)

Guidance literature:

Multi-step reaction with 6 steps

1: toluene / Heating

2: AgOAc / CH₂Cl₂

3: (H₂N)2C=S, pyridine / dimethylformamide

4: Cl(CO)2Cl, DMSO

5: LiClO₄ / acetonitrile

6: MCPBA

With pyridine; oxalyl dichloride; silver(I) acetate; lithium perchlorate; dimethyl sulfoxide; thiourea; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0960-894X(99)00325-X

upstream raw materials:

(2S,3S,5R)-6-[1-tert-Butoxycarbonyl-meth-(Z)-ylidene]-3-((Z)-2-cyano-vinyl)-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

benzhydryl 6-oxopenicillinate

benzhydryl 6-(Z)-(1-tert-butoxycarbonylmethylene)penicillanate

(2S,4R,5R)-6-[1-tert-Butoxycarbonyl-meth-(Z)-ylidene]-3,3-dimethyl-4,7-dioxo-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

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