[2-(2-Acetoxy-ethylsulfanylthiocarbonylsulfanyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-nitro-benzyl ester

Base Information

• Chemical Name: [2-(2-Acetoxy-ethylsulfanylthiocarbonylsulfanyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-nitro-benzyl ester
• CAS No.: 77597-18-3
• Molecular Formula: C₃₅H₃₁N₂O₇PS₃
• Molecular Weight: 718.812

Synonyms:[2-(2-Acetoxy-ethylsulfanylthiocarbonylsulfanyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-nitro-benzyl ester

Chemical Property of [2-(2-Acetoxy-ethylsulfanylthiocarbonylsulfanyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-nitro-benzyl ester

Chemical Property:

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Technology Process of [2-(2-Acetoxy-ethylsulfanylthiocarbonylsulfanyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-nitro-benzyl ester

There total 9 articles about [2-(2-Acetoxy-ethylsulfanylthiocarbonylsulfanyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-nitro-benzyl 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:

[2-(2-Acetoxy-ethylsulfanylthiocarbonylsulfanyl)-4-oxo-azetidin-1-yl]-chloro-acetic acid 4-nitro-benzyl ester + triphenylphosphine (603-35-0) → [2-(2-Acetoxy-ethylsulfanylthiocarbonylsulfanyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid 4-nitro-benzyl ester (77597-18-3)

Guidance literature:

With 2,6-dimethylpyridine; In tetrahydrofuran; at 60 ℃; for 12h; Yield given;

DOI:10.1248/cpb.28.3232

Reference yield:

4-<<<<2-<(tetrahydropyran-2-yl)oxy>ethyl>thio>thiocarbonyl>thio>-2-azetidinone (77597-10-5) → [2-(2-Acetoxy-ethylsulfanylthiocarbonylsulfanyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid 4-nitro-benzyl ester (77597-18-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / benzene / 9 h / Heating

2: 1.) 2,6-lutidine, thionyl chloride; 2.) 2,6-lutidine / 1.) THF, -10 deg C, 30 min; 2.) THF, -10 deg C, then 50 deg C, 11 h

3: 98 percent / p-toluenesulfonic acid (hydrate) / tetrahydrofuran; H₂O / 7 h / 50 °C

4: Et₃N / CH₂Cl₂

With 2,6-dimethylpyridine; thionyl chloride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; dichloromethane; water; benzene;

Reference yield:

Hydroxy-{2-oxo-4-[2-(tetrahydro-pyran-2-yloxy)-ethylsulfanylthiocarbonylsulfanyl]-azetidin-1-yl}-acetic acid 4-nitro-benzyl ester (77597-12-7) → [2-(2-Acetoxy-ethylsulfanylthiocarbonylsulfanyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid 4-nitro-benzyl ester (77597-18-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) 2,6-lutidine, thionyl chloride; 2.) 2,6-lutidine / 1.) THF, -10 deg C, 30 min; 2.) THF, -10 deg C, then 50 deg C, 11 h

2: 98 percent / p-toluenesulfonic acid (hydrate) / tetrahydrofuran; H₂O / 7 h / 50 °C

3: Et₃N / CH₂Cl₂

With 2,6-dimethylpyridine; thionyl chloride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; dichloromethane; water;

upstream raw materials:

acetic anhydride

p-nitrobenzyl 2-<4-<<<(2-hydroxyethyl)thio>thiocarbonyl>thio>-2-oxo-1-azetidinyl>-2-(triphenylphosphoranylidene)acetate

triphenylphosphine

4-<<<<2-<(tetrahydropyran-2-yl)oxy>ethyl>thio>thiocarbonyl>thio>-2-azetidinone

Downstream raw materials:

3-(2-Acetoxy-ethylsulfanyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

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