3-{1-[(4-Nitro-benzyloxycarbonyl)-(triphenyl-λ⁵-phosphanylidene)-methyl]-4-oxo-azetidin-2-ylsulfanylthiocarbonylsulfanyl}-propionic acid ethyl ester

Base Information

• Chemical Name: 3-{1-[(4-Nitro-benzyloxycarbonyl)-(triphenyl-λ⁵-phosphanylidene)-methyl]-4-oxo-azetidin-2-ylsulfanylthiocarbonylsulfanyl}-propionic acid ethyl ester
• CAS No.: 77705-09-0
• Molecular Formula: C₃₆H₃₃N₂O₇PS₃
• Molecular Weight: 732.839

Synonyms:3-{1-[(4-Nitro-benzyloxycarbonyl)-(triphenyl-λ⁵-phosphanylidene)-methyl]-4-oxo-azetidin-2-ylsulfanylthiocarbonylsulfanyl}-propionic acid ethyl ester

Chemical Property of 3-{1-[(4-Nitro-benzyloxycarbonyl)-(triphenyl-λ⁵-phosphanylidene)-methyl]-4-oxo-azetidin-2-ylsulfanylthiocarbonylsulfanyl}-propionic acid ethyl ester

Chemical Property:

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Technology Process of 3-{1-[(4-Nitro-benzyloxycarbonyl)-(triphenyl-λ⁵-phosphanylidene)-methyl]-4-oxo-azetidin-2-ylsulfanylthiocarbonylsulfanyl}-propionic acid ethyl ester

There total 4 articles about 3-{1-[(4-Nitro-benzyloxycarbonyl)-(triphenyl-λ⁵-phosphanylidene)-methyl]-4-oxo-azetidin-2-ylsulfanylthiocarbonylsulfanyl}-propionic acid ethyl 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:

3-{1-[Chloro-(4-nitro-benzyloxycarbonyl)-methyl]-4-oxo-azetidin-2-ylsulfanylthiocarbonylsulfanyl}-propionic acid ethyl ester + triphenylphosphine (603-35-0) → 3-{1-[(4-Nitro-benzyloxycarbonyl)-(triphenyl-λ5-phosphanylidene)-methyl]-4-oxo-azetidin-2-ylsulfanylthiocarbonylsulfanyl}-propionic acid ethyl ester (77705-09-0)

Guidance literature:

With 2,6-dimethylpyridine; In tetrahydrofuran; at 55 ℃; for 12h; Yield given;

DOI:10.1248/cpb.28.3232

Reference yield:

3-mercaptopropionic acid ethyl ester (5466-06-8) → 3-{1-[(4-Nitro-benzyloxycarbonyl)-(triphenyl-λ5-phosphanylidene)-methyl]-4-oxo-azetidin-2-ylsulfanylthiocarbonylsulfanyl}-propionic acid ethyl ester (77705-09-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 60 percent / sodium methoxide / methanol / 1.5 h / Ambient temperature

2: 95 percent / benzene / 1.5 h / Heating

3: 2,6-lutidine, thionyl chloride / tetrahydrofuran / 0.33 h / -15 °C

4: 2,6-lutidine / tetrahydrofuran / 12 h / 55 °C

With 2,6-dimethylpyridine; thionyl chloride; sodium methylate; In tetrahydrofuran; methanol; benzene;

DOI:10.1248/cpb.28.3232

Reference yield:

3-(4-Oxo-azetidin-2-ylsulfanylthiocarbonylsulfanyl)-propionic acid ethyl ester (77704-91-7) → 3-{1-[(4-Nitro-benzyloxycarbonyl)-(triphenyl-λ5-phosphanylidene)-methyl]-4-oxo-azetidin-2-ylsulfanylthiocarbonylsulfanyl}-propionic acid ethyl ester (77705-09-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / benzene / 1.5 h / Heating

2: 2,6-lutidine, thionyl chloride / tetrahydrofuran / 0.33 h / -15 °C

3: 2,6-lutidine / tetrahydrofuran / 12 h / 55 °C

With 2,6-dimethylpyridine; thionyl chloride; In tetrahydrofuran; benzene;

DOI:10.1248/cpb.28.3232

upstream raw materials:

triphenylphosphine

3-mercaptopropionic acid ethyl ester

3-(4-Oxo-azetidin-2-ylsulfanylthiocarbonylsulfanyl)-propionic acid ethyl ester

3-{1-[Hydroxy-(4-nitro-benzyloxycarbonyl)-methyl]-4-oxo-azetidin-2-ylsulfanylthiocarbonylsulfanyl}-propionic acid ethyl ester

Downstream raw materials:

3-(2-Ethoxycarbonyl-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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