(R)-3-Fluoro-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-Fluoro-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.: 371207-94-2
• Molecular Formula: C₂₆H₁₉FN₂O₅S
• Molecular Weight: 490.512

Synonyms:(R)-3-Fluoro-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 of (R)-3-Fluoro-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:

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Technology Process of (R)-3-Fluoro-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 8 articles about (R)-3-Fluoro-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: 42.0%

(R)-5,5,8-Trioxo-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-3-trimethylstannanyl-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester → (R)-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 (371207-96-4) + (R)-3-Fluoro-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 (371207-94-2)

Guidance literature:

With xenon difluoride; silver trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.0833333h;

DOI:10.1021/ol016142v

Reference yield:

(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 (371207-64-6) → (R)-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 (371207-96-4) + (R)-3-Fluoro-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 (371207-94-2)

Guidance literature:

(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; With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; hexamethyldistannane; In tetrahydrofuran;

With xenon difluoride; silver trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.0833333h;

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

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-Fluoro-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 (371207-94-2)

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: (Me₃Sn)2; Pd₂(dba)3 / tetrahydrofuran

7.2: XeF₂; AgOTf / CH₂Cl₂ / 0.08 h / 0 °C

With pyridine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; i-propyl nitrite; phosphorus pentachloride; potassium tert-butylate; hexamethyldistannane; 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

upstream raw materials:

(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

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

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