(3R,4S)-1-(4-Methoxy-phenyl)-4-phenyl-3-((1S,3R,6R)-3,7,7-trimethyl-4-oxo-bicyclo[4.1.0]hept-3-yloxy)-azetidin-2-one

Base Information

• Chemical Name: (3R,4S)-1-(4-Methoxy-phenyl)-4-phenyl-3-((1S,3R,6R)-3,7,7-trimethyl-4-oxo-bicyclo[4.1.0]hept-3-yloxy)-azetidin-2-one
• CAS No.: 176656-93-2
• Molecular Formula: C₂₆H₂₉NO₄
• Molecular Weight: 419.521
• Mol file: 176656-93-2.mol

Synonyms:(3R,4S)-1-(4-Methoxy-phenyl)-4-phenyl-3-((1S,3R,6R)-3,7,7-trimethyl-4-oxo-bicyclo[4.1.0]hept-3-yloxy)-azetidin-2-one

Chemical Property of (3R,4S)-1-(4-Methoxy-phenyl)-4-phenyl-3-((1S,3R,6R)-3,7,7-trimethyl-4-oxo-bicyclo[4.1.0]hept-3-yloxy)-azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-1-(4-Methoxy-phenyl)-4-phenyl-3-((1S,3R,6R)-3,7,7-trimethyl-4-oxo-bicyclo[4.1.0]hept-3-yloxy)-azetidin-2-one

There total 3 articles about (3R,4S)-1-(4-Methoxy-phenyl)-4-phenyl-3-((1S,3R,6R)-3,7,7-trimethyl-4-oxo-bicyclo[4.1.0]hept-3-yloxy)-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: 57.0%

[4-(benzylideneamino)phenyl]methanol (783-08-4) + ((1S,3R,6R)-3,7,7-Trimethyl-4-oxo-bicyclo[4.1.0]hept-3-yloxy)-acetic acid (176656-92-1) → (3S,4R)-1-(4-Methoxy-phenyl)-4-phenyl-3-((1S,3R,6R)-3,7,7-trimethyl-4-oxo-bicyclo[4.1.0]hept-3-yloxy)-azetidin-2-one + (3R,4S)-1-(4-Methoxy-phenyl)-4-phenyl-3-((1S,3R,6R)-3,7,7-trimethyl-4-oxo-bicyclo[4.1.0]hept-3-yloxy)-azetidin-2-one (176656-93-2)

Guidance literature:

With O-phenyl phosphorodichloridate; triethylamine; In dichloromethane; for 15h; Yield given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1016/0040-4020(96)00200-1

Reference yield:

(1R,3R,4R,6S)-4-(2-Hydroxy-ethoxy)-4,7,7-trimethyl-bicyclo[4.1.0]heptan-3-ol (176656-91-0) → (3R,4S)-1-(4-Methoxy-phenyl)-4-phenyl-3-((1S,3R,6R)-3,7,7-trimethyl-4-oxo-bicyclo[4.1.0]hept-3-yloxy)-azetidin-2-one (176656-93-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / Jones' reagent / acetone / 4 h / Ambient temperature

2: 57 percent / Et₃N, phenyl dichlorophosphate / CH₂Cl₂ / 15 h / Ambient temperature

With jones' reagent; O-phenyl phosphorodichloridate; triethylamine; In dichloromethane; acetone;

DOI:10.1016/0040-4020(96)00200-1

Reference yield:

3-carene epoxide (936-91-4) → (3R,4S)-1-(4-Methoxy-phenyl)-4-phenyl-3-((1S,3R,6R)-3,7,7-trimethyl-4-oxo-bicyclo[4.1.0]hept-3-yloxy)-azetidin-2-one (176656-93-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / PTSA / 4 h / 0 °C

2: 77 percent / Jones' reagent / acetone / 4 h / Ambient temperature

3: 57 percent / Et₃N, phenyl dichlorophosphate / CH₂Cl₂ / 15 h / Ambient temperature

With jones' reagent; toluene-4-sulfonic acid; O-phenyl phosphorodichloridate; triethylamine; In dichloromethane; acetone;

DOI:10.1016/0040-4020(96)00200-1

upstream raw materials:

[4-(benzylideneamino)phenyl]methanol

((1S,3R,6R)-3,7,7-Trimethyl-4-oxo-bicyclo[4.1.0]hept-3-yloxy)-acetic acid

(1R,3R,4R,6S)-4-(2-Hydroxy-ethoxy)-4,7,7-trimethyl-bicyclo[4.1.0]heptan-3-ol

3-carene epoxide

Downstream raw materials:

(3R,4S)-(+)-3-hydroxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone