(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-formyl-azetidin-2-one

Base Information

• Chemical Name: (3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-formyl-azetidin-2-one
• CAS No.: 1240816-59-4
• Molecular Formula: C₂₃H₁₈FNO₃
• Molecular Weight: 375.399
• Mol file: 1240816-59-4.mol

Synonyms:(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-formyl-azetidin-2-one

Chemical Property of (3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-formyl-azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-formyl-azetidin-2-one

There total 6 articles about (3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-formyl-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:

(3R,4S)-4-(4-(benzyloxy)phenyl)-3-((1'R)-1',2'-dihydroxyethyl)-1-(4-fluorophenyl)-azetidin-2-one (1240816-39-0) → (3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-formyl-azetidin-2-one (1240816-59-4)

Guidance literature:

With sodium periodate; sodium hydrogencarbonate; In water; acetonitrile; at 5 ℃;

Reference yield:

(3R,4S)-4-(4-(benzyloxy)phenyl)-3-((1'R)-1',2'-dihydroxyethyl)-1-(4-fluorophenyl)-azetidin-2-one (1240816-39-0) → (3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-formyl-azetidin-2-one (1240816-59-4) + (2S,3S)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxazetidine-3-carbaldehyde (221349-58-2)

Guidance literature:

(3R,4S)-4-(4-(benzyloxy)phenyl)-3-((1'R)-1',2'-dihydroxyethyl)-1-(4-fluorophenyl)-azetidin-2-one; With SiO₂-supported NaIO₄; In dichloromethane; at 0 ℃; for 2h;

With sodium hydrogencarbonate; In dichloromethane; at 0 ℃; for 3h; optical yield given as %de;

DOI:10.1021/jo2010846

Reference yield:

N-(4-fluorophenyl)-α-(4-benzyloxyphenyl)nitrone (1240815-99-9) → (3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-formyl-azetidin-2-one (1240816-59-4) + (2S,3S)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxazetidine-3-carbaldehyde (221349-58-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: copper(l) iodide; N,N,N',N'-tetramethylguanidine / acetonitrile / 0 °C / Inert atmosphere

1.2: 16 h / 20 °C / Inert atmosphere

2.1: water; trifluoroacetic acid / tetrahydrofuran / 6 h / 50 °C

3.1: SiO₂-supported NaIO₄ / dichloromethane / 2 h / 0 °C

3.2: 3 h / 0 °C

With copper(l) iodide; SiO₂-supported NaIO₄; water; trifluoroacetic acid; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; dichloromethane; acetonitrile; 1.2: Kinugasa reaction;

DOI:10.1021/jo2010846

upstream raw materials:

(3R,4S)-4-(4-(benzyloxy)phenyl)-3-((1'R)-1',2'-dihydroxyethyl)-1-(4-fluorophenyl)-azetidin-2-one

N-(4-fluorophenyl)-α-(4-benzyloxyphenyl)nitrone

(3R,4S)-4-(4-(benzyloxy)phenyl)-3-((4'R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-(4-fluorophenyl)azetidin-2-one

4-fluoro-N-hydroxyaniline

Downstream raw materials:

(2S,3S)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxazetidine-3-carbaldehyde