(R)-5,5,8-Trioxo-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-3-((E)-2-pyridin-2-yl-vinyl)-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Base Information

• Chemical Name: (R)-5,5,8-Trioxo-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-3-((E)-2-pyridin-2-yl-vinyl)-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
• CAS No.: 302566-19-4
• Molecular Formula: C₃₃H₂₅N₃O₅S
• Molecular Weight: 575.645

Synonyms:

Chemical Property of (R)-5,5,8-Trioxo-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-3-((E)-2-pyridin-2-yl-vinyl)-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-5,5,8-Trioxo-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-3-((E)-2-pyridin-2-yl-vinyl)-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

There total 10 articles about (R)-5,5,8-Trioxo-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-3-((E)-2-pyridin-2-yl-vinyl)-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:

(R)-8-Oxo-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-3-((E)-2-pyridin-2-yl-vinyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (287489-10-5) → (R)-5,5,8-Trioxo-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-3-((E)-2-pyridin-2-yl-vinyl)-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (302566-19-4)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 0.5h; pH=6.4;

DOI:10.1016/S0960-894X(00)00094-9

Reference yield:

(6R,7R)-benzhydryl 3-(hydroxymethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (35246-64-1) → (R)-5,5,8-Trioxo-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-3-((E)-2-pyridin-2-yl-vinyl)-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (302566-19-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: pyridine / CH₂Cl₂ / 12 h / 20 °C

2.1: PCl₅; pyridine / CH₂Cl₂ / 3 h / 0 °C

3.1: i-pr-ONO; TFA

3.2: propylene oxide; RH₂(OOct)4

4.1: tetrahydrofuran / -78 °C

5.1: (n-Bu)3SnH; Pd(PPh₃)4 / CH₂Cl₂ / 0.25 h / 0 °C

6.1: pyridinium dichromate / CH₂Cl₂ / 6 h / 20 °C

7.1: tetrahydrofuran / 20 h / 20 °C

8.1: mCPBA / CH₂Cl₂ / 0.5 h / 0 °C / pH 6.4

With pyridine; dipyridinium dichromate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; i-propyl nitrite; phosphorus pentachloride; tri-n-butyl-tin hydride; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; 1.1: Acylation / 2.1: deacylation / 3.1: Diazotization / 3.2: Oxidation / 4.1: Condensation / 5.1: deacylation / 6.1: Oxidation / 7.1: Wittig reaction / 8.1: Oxidation;

DOI:10.1016/S0960-894X(00)00094-9

Reference yield:

(6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (15690-38-7) → (R)-5,5,8-Trioxo-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-3-((E)-2-pyridin-2-yl-vinyl)-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (302566-19-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: Et₃N

3.1: pyridine / CH₂Cl₂ / 12 h / 20 °C

4.1: PCl₅; pyridine / CH₂Cl₂ / 3 h / 0 °C

5.1: i-pr-ONO; TFA

5.2: propylene oxide; RH₂(OOct)4

6.1: tetrahydrofuran / -78 °C

7.1: (n-Bu)3SnH; Pd(PPh₃)4 / CH₂Cl₂ / 0.25 h / 0 °C

8.1: pyridinium dichromate / CH₂Cl₂ / 6 h / 20 °C

9.1: tetrahydrofuran / 20 h / 20 °C

10.1: mCPBA / CH₂Cl₂ / 0.5 h / 0 °C / pH 6.4

With pyridine; dipyridinium dichromate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; i-propyl nitrite; phosphorus pentachloride; tri-n-butyl-tin hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; 1.1: Acylation / 2.1: Esterification / 3.1: Acylation / 4.1: deacylation / 5.1: Diazotization / 5.2: Oxidation / 6.1: Condensation / 7.1: deacylation / 8.1: Oxidation / 9.1: Wittig reaction / 10.1: Oxidation;

DOI:10.1016/S0960-894X(00)00094-9

upstream raw materials:

(R)-8-Oxo-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-3-((E)-2-pyridin-2-yl-vinyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

(6R,7R)-benzhydryl 3-(hydroxymethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

(6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

3-hydroxymethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

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