(+/-)-3α-<(1R^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-1--4β-<(phenylthio)carbonylmethyl>azetidin-2-one

Base Information

• Chemical Name: (+/-)-3α-<(1R^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-1--4β-<(phenylthio)carbonylmethyl>azetidin-2-one
• CAS No.: 78072-34-1
• Molecular Formula: C₄₈H₄₀N₃O₁₁PS
• Molecular Weight: 897.899

Synonyms:

Chemical Property of (+/-)-3α-<(1R^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-1--4β-<(phenylthio)carbonylmethyl>azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of (+/-)-3α-<(1R^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-1--4β-<(phenylthio)carbonylmethyl>azetidin-2-one

There total 8 articles about (+/-)-3α-<(1R^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-1--4β-<(phenylthio)carbonylmethyl>azetidin-2-one 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:

(3S,4R)-4-(2,2-dimethoxyethyl)-3-[(1RS)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-2-oxoazetidine (72789-82-3,72843-58-4,73890-31-0,73890-76-3,77447-98-4,78342-09-3,78822-11-4,79057-48-0,79299-23-3,79952-71-9) → (+/-)-3α-<(1R*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-1--4β-<(phenylthio)carbonylmethyl>azetidin-2-one (78072-34-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 80percent aq. acetic acid / 4 h / 55 - 60 °C

2: 1.40 g / 8N Jones reagent / acetone / 0 °C

3: 97 mg / 4-dimethylaminopyridine, NN'-dicyclohexylcarbodi-imide / CH₂Cl₂ / 1.) 0 deg C, 30 min, 2.) room temperature, 3 h

4: 1.24 g / activated molecular sieves / toluene; dimethylformamide / 1.) room temperature, 12 h, 2.) 50 deg C, 5 h

5: 2,6-lutidine, thionyl chloride / tetrahydrofuran / -15 deg C to room temperature, 30 min

6: 64.5 mg / 2,6-lutidine / dioxane / 1.) room temperature, 15 h, 2.) 50 deg C, 15 h

With 2,6-dimethylpyridine; dmap; thionyl chloride; jones reagent; acetic acid; dicyclohexyl-carbodiimide; molecular sieve; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1039/P19810000964

Reference yield:

p-nitrobenzyl α-ethoxy-α-hydroxyacetate (64370-36-1) → (+/-)-3α-<(1R*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-1--4β-<(phenylthio)carbonylmethyl>azetidin-2-one (78072-34-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.24 g / activated molecular sieves / toluene; dimethylformamide / 1.) room temperature, 12 h, 2.) 50 deg C, 5 h

2: 2,6-lutidine, thionyl chloride / tetrahydrofuran / -15 deg C to room temperature, 30 min

3: 64.5 mg / 2,6-lutidine / dioxane / 1.) room temperature, 15 h, 2.) 50 deg C, 15 h

With 2,6-dimethylpyridine; thionyl chloride; molecular sieve; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; toluene;

DOI:10.1039/P19810000964

Reference yield:

thiophenol (108-98-5) → (+/-)-3α-<(1R*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-1--4β-<(phenylthio)carbonylmethyl>azetidin-2-one (78072-34-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 mg / 4-dimethylaminopyridine, NN'-dicyclohexylcarbodi-imide / CH₂Cl₂ / 1.) 0 deg C, 30 min, 2.) room temperature, 3 h

2: 1.24 g / activated molecular sieves / toluene; dimethylformamide / 1.) room temperature, 12 h, 2.) 50 deg C, 5 h

3: 2,6-lutidine, thionyl chloride / tetrahydrofuran / -15 deg C to room temperature, 30 min

4: 64.5 mg / 2,6-lutidine / dioxane / 1.) room temperature, 15 h, 2.) 50 deg C, 15 h

With 2,6-dimethylpyridine; dmap; thionyl chloride; dicyclohexyl-carbodiimide; molecular sieve; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1039/P19810000964

upstream raw materials:

triphenylphosphine

(3S,4R)-4-(2,2-dimethoxyethyl)-3-[(1RS)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-2-oxoazetidine

p-nitrobenzyl α-ethoxy-α-hydroxyacetate

thiophenol

Downstream raw materials:

(+/-)-p-nitrobenzyl 6α-<(1R^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-3-phenylthio-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

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