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

Base Information

• Chemical Name: (R)-3-Methylsulfanyl-5,5,8-trioxo-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
• CAS No.: 460739-00-8
• Molecular Formula: C₂₇H₂₂N₂O₅S₂
• Molecular Weight: 518.614

Synonyms:

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

There total 7 articles about (R)-3-Methylsulfanyl-5,5,8-trioxo-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-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:

(6R,7R)-benzhydryl 3-hydroxy-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (54639-48-4) → (R)-3-Methylsulfanyl-5,5,8-trioxo-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (460739-00-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 85 percent / DIPEA / CH₂Cl₂ / -78 °C

2.1: LiI / tetrahydrofuran / 36 h / 20 °C

3.1: 74 percent / PCl₅; pyridine / methanol; CH₂Cl₂ / 0 °C

4.1: i-prONO; TFA / ethyl acetate

4.2: propylene oxide; Rh₂(OOct)4 / benzene

5.1: KO-t-Bu / tetrahydrofuran; CH₂Cl₂

6.1: 90 percent / mCPBA / CH₂Cl₂ / 0.5 h / 20 °C

7.1: Pd₂(dba)3

With pyridine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; i-propyl nitrite; phosphorus pentachloride; potassium tert-butylate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; lithium iodide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;

DOI:10.1016/S0960-894X(02)00205-6

Reference yield:

(6R,7R)-3-Iodo-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (123054-35-3) → (R)-3-Methylsulfanyl-5,5,8-trioxo-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (460739-00-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 74 percent / PCl₅; pyridine / methanol; CH₂Cl₂ / 0 °C

2.1: i-prONO; TFA / ethyl acetate

2.2: propylene oxide; Rh₂(OOct)4 / benzene

3.1: KO-t-Bu / tetrahydrofuran; CH₂Cl₂

4.1: 90 percent / mCPBA / CH₂Cl₂ / 0.5 h / 20 °C

5.1: Pd₂(dba)3

With pyridine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; i-propyl nitrite; phosphorus pentachloride; potassium tert-butylate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;

DOI:10.1016/S0960-894X(02)00205-6

Reference yield:

(6R,7R)-benzhydryl 8-oxo-7-(2-phenylacetamido)-3-(((trifluoromethyl)sulfonyl)oxy)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (122553-60-0) → (R)-3-Methylsulfanyl-5,5,8-trioxo-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (460739-00-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: LiI / tetrahydrofuran / 36 h / 20 °C

2.1: 74 percent / PCl₅; pyridine / methanol; CH₂Cl₂ / 0 °C

3.1: i-prONO; TFA / ethyl acetate

3.2: propylene oxide; Rh₂(OOct)4 / benzene

4.1: KO-t-Bu / tetrahydrofuran; CH₂Cl₂

5.1: 90 percent / mCPBA / CH₂Cl₂ / 0.5 h / 20 °C

6.1: Pd₂(dba)3

With pyridine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; i-propyl nitrite; phosphorus pentachloride; potassium tert-butylate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; lithium iodide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;

DOI:10.1016/S0960-894X(02)00205-6

upstream raw materials:

tributyl(methylthio)stannane

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

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

(6R,7R)-3-Iodo-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Downstream raw materials:

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

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