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

Base Information

• Chemical Name: 3-{1-[(4-Nitro-benzyloxycarbonyl)-(triphenyl-λ⁵-phosphanylidene)-methyl]-4-oxo-azetidin-2-ylsulfanylthiocarbonylsulfanyl}-propionic acid 4-nitro-benzyl ester
• CAS No.: 77705-11-4
• Molecular Formula: C₄₁H₃₄N₃O₉PS₃
• Molecular Weight: 839.907

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

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

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

3-{1-[Chloro-(4-nitro-benzyloxycarbonyl)-methyl]-4-oxo-azetidin-2-ylsulfanylthiocarbonylsulfanyl}-propionic acid 4-nitro-benzyl ester + triphenylphosphine (603-35-0) → 3-{1-[(4-Nitro-benzyloxycarbonyl)-(triphenyl-λ5-phosphanylidene)-methyl]-4-oxo-azetidin-2-ylsulfanylthiocarbonylsulfanyl}-propionic acid 4-nitro-benzyl ester (77705-11-4)

Guidance literature:

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

DOI:10.1248/cpb.28.3232

Reference yield:

p-nitrobenzyl β-mercaptopropionate (77705-29-4) → 3-{1-[(4-Nitro-benzyloxycarbonyl)-(triphenyl-λ5-phosphanylidene)-methyl]-4-oxo-azetidin-2-ylsulfanylthiocarbonylsulfanyl}-propionic acid 4-nitro-benzyl ester (77705-11-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 41 percent / sodium methoxide / methanol / 0.67 h / Ambient temperature

2: 79 percent / benzene / 5.5 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 4-nitro-benzyl ester (77704-93-9) → 3-{1-[(4-Nitro-benzyloxycarbonyl)-(triphenyl-λ5-phosphanylidene)-methyl]-4-oxo-azetidin-2-ylsulfanylthiocarbonylsulfanyl}-propionic acid 4-nitro-benzyl ester (77705-11-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 79 percent / benzene / 5.5 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

p-nitrobenzyl β-mercaptopropionate

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

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

Downstream raw materials:

3-[2-(4-Nitro-benzyloxycarbonyl)-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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