(Z)-2-(Diphenoxy-phosphoryloxy)-3-((2S,3R)-3-ethyl-4-oxo-azetidin-2-ylsulfanyl)-but-2-enedioic acid 1-benzyl ester 4-ethyl ester

Base Information

• Chemical Name: (Z)-2-(Diphenoxy-phosphoryloxy)-3-((2S,3R)-3-ethyl-4-oxo-azetidin-2-ylsulfanyl)-but-2-enedioic acid 1-benzyl ester 4-ethyl ester
• CAS No.: 100044-53-9
• Molecular Formula: C₃₀H₃₀NO₉PS
• Molecular Weight: 611.609
• Mol file: 100044-53-9.mol

Synonyms:(Z)-2-(Diphenoxy-phosphoryloxy)-3-((2S,3R)-3-ethyl-4-oxo-azetidin-2-ylsulfanyl)-but-2-enedioic acid 1-benzyl ester 4-ethyl ester

Chemical Property of (Z)-2-(Diphenoxy-phosphoryloxy)-3-((2S,3R)-3-ethyl-4-oxo-azetidin-2-ylsulfanyl)-but-2-enedioic acid 1-benzyl ester 4-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-2-(Diphenoxy-phosphoryloxy)-3-((2S,3R)-3-ethyl-4-oxo-azetidin-2-ylsulfanyl)-but-2-enedioic acid 1-benzyl ester 4-ethyl ester

There total 6 articles about (Z)-2-(Diphenoxy-phosphoryloxy)-3-((2S,3R)-3-ethyl-4-oxo-azetidin-2-ylsulfanyl)-but-2-enedioic acid 1-benzyl ester 4-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: 69.7%

2-((2R,3S)-3-Ethyl-4-oxo-azetidin-2-ylsulfanyl)-3-oxo-succinic acid 4-benzyl ester 1-ethyl ester (100044-51-7) + chlorophosphoric acid diphenyl ester (2524-64-3) → (Z)-2-(Diphenoxy-phosphoryloxy)-3-((2S,3R)-3-ethyl-4-oxo-azetidin-2-ylsulfanyl)-but-2-enedioic acid 1-benzyl ester 4-ethyl ester (100044-53-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1021/jo00355a011

Reference yield:

dibenzyl oxalate (7579-36-4) → (Z)-2-(Diphenoxy-phosphoryloxy)-3-((2S,3R)-3-ethyl-4-oxo-azetidin-2-ylsulfanyl)-but-2-enedioic acid 1-benzyl ester 4-ethyl ester (100044-53-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) lithium hexamethyldisilazide / 1.) THF, -78 deg C, 0.1 h, 2.) THF, RT, 2 h

2: 72 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / Ambient temperature

3: 69.7 percent / diisopropylethylamine / CH₂Cl₂ / 3 h / 0 °C

With tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00355a011

Reference yield:

4-acetoxy-3-ethyl-azetidin-2-one (82290-86-6) → (Z)-2-(Diphenoxy-phosphoryloxy)-3-((2S,3R)-3-ethyl-4-oxo-azetidin-2-ylsulfanyl)-but-2-enedioic acid 1-benzyl ester 4-ethyl ester (100044-53-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / KOH / ethanol; H₂O / 0.5 h

2: 1.) lithium hexamethyldisilazide / 1.) THF, -78 deg C, 5 min, 2.) THF, from -78 deg C to 0 deg C, 1.5 h

3: 1.) lithium hexamethyldisilazide / 1.) THF, -78 deg C, 0.1 h, 2.) THF, RT, 2 h

4: 72 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / Ambient temperature

5: 69.7 percent / diisopropylethylamine / CH₂Cl₂ / 3 h / 0 °C

With potassium hydroxide; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; water;

DOI:10.1021/jo00355a011

upstream raw materials:

2-((2R,3S)-3-Ethyl-4-oxo-azetidin-2-ylsulfanyl)-3-oxo-succinic acid 4-benzyl ester 1-ethyl ester

chlorophosphoric acid diphenyl ester

dibenzyl oxalate

4-acetoxy-3-ethyl-azetidin-2-one

Refernces