(6R,7R)-7-tert-Butoxycarbonylamino-8-oxo-3-[(triphenyl-λ⁵-phosphanylidene)-methyl]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Base Information

• Chemical Name: (6R,7R)-7-tert-Butoxycarbonylamino-8-oxo-3-[(triphenyl-λ⁵-phosphanylidene)-methyl]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
• CAS No.: 143159-43-7
• Molecular Formula: C₄₄H₄₁N₂O₅PS
• Molecular Weight: 740.86

Synonyms:

Chemical Property of (6R,7R)-7-tert-Butoxycarbonylamino-8-oxo-3-[(triphenyl-λ⁵-phosphanylidene)-methyl]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Chemical Property:

Purity/Quality:

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Technology Process of (6R,7R)-7-tert-Butoxycarbonylamino-8-oxo-3-[(triphenyl-λ⁵-phosphanylidene)-methyl]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

There total 1 articles about (6R,7R)-7-tert-Butoxycarbonylamino-8-oxo-3-[(triphenyl-λ⁵-phosphanylidene)-methyl]-5-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:

diphenylmethyl 7β-tert-butoxycarbonylamino-3-triphenylphosphoniomethyl-3-cephem-4-carboxylate iodide → (6R,7R)-7-tert-Butoxycarbonylamino-8-oxo-3-[(triphenyl-λ5-phosphanylidene)-methyl]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (143159-43-7)

Guidance literature:

With sodium hydroxide; sodium chloride; In dichloromethane; water; at 20 ℃; for 0.75h;

DOI:10.1016/S0968-0896(99)00257-6

Reference yield: 32.0%

1-phenylazetidine-2,3-dione (161674-42-6) + (6R,7R)-7-tert-Butoxycarbonylamino-8-oxo-3-[(triphenyl-λ5-phosphanylidene)-methyl]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (143159-43-7) → (2R,6R,7R)-7-tert-Butoxycarbonylamino-8-oxo-3-[2-oxo-1-phenyl-azetidin-(3E)-ylidenemethyl]-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid benzhydryl ester + (6R,7R)-7-tert-Butoxycarbonylamino-8-oxo-3-[2-oxo-1-phenyl-azetidin-(3Z)-ylidenemethyl]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester + (E)-(6R,7R)-7-tert-butoxycarbonyl-amino-8-oxo-3-(2-oxo-1-phenyl-azetidin-3-ylidenemethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (161674-83-5)

Guidance literature:

In various solvent(s); for 1.5h; Ambient temperature;

DOI:10.1021/jm950886v

Reference yield:

(6R,7R)-7-tert-Butoxycarbonylamino-8-oxo-3-[(triphenyl-λ5-phosphanylidene)-methyl]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (143159-43-7) → pivaloyloxymethyl 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-[(Z)-2-(pyridin-3-yl)vinyl]-3-cephem-4-carboxylate (159296-78-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 21.0 g / CH₂Cl₂ / 20 h / 20 °C

2.1: 74 percent / conc. HCl / formic acid / 2 h / 20 °C

3.1: Et₃N; trimethylsilyl chloride / tetrahydrofuran / 0.5 h / 20 °C

3.2: 50 percent / tetrahydrofuran; dimethylformamide / 20 °C

4.1: 19 percent / K₂CO₃ / dimethylformamide / 0.5 h / 0 °C

With hydrogenchloride; chloro-trimethyl-silane; potassium carbonate; triethylamine; In tetrahydrofuran; formic acid; dichloromethane; N,N-dimethyl-formamide; 1.1: Wittig reaction / 2.1: Hydrolysis / 3.1: silylation / 3.2: Acylation / 4.1: Substitution;

DOI:10.1016/S0968-0896(99)00257-6

Downstream raw materials:

(E)-(6R,7R)-7-tert-butoxycarbonyl-amino-8-oxo-3-(2-oxo-1-phenyl-azetidin-3-ylidenemethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

diphenylmethyl 7β-tert-butoxycarbonylamino-3-[(Z)-2-(pyridin-4-yl)vinyl]-3-cephem-4-carboxylate

diphenylmethyl 7β-tert-butoxycarbonylamino-3-[(Z)-2-(pyridin-3-yl)vinyl]-3-cephem-4-carboxylate

diphenylmethyl 7β-tert-butoxycarbonylamino-3-[(E)-2-(pyridin-3-yl)vinyl]-3-cephem-4-carboxylate

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