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

Base Information

• Chemical Name: (3R,4S)-4-(4-(benzyloxy)phenyl)-3-((4'R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-(4-fluorophenyl)azetidin-2-one
• CAS No.: 1240816-36-7
• Molecular Formula: C₂₇H₂₆FNO₄
• Molecular Weight: 447.506
• Mol file: 1240816-36-7.mol

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

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

There total 4 articles about (3R,4S)-4-(4-(benzyloxy)phenyl)-3-((4'R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-(4-fluorophenyl)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: 70.0%

(Z)-N-(4-(benzyloxy)benzylidene)-4-fluoroaniline-N-oxide (1240815-99-9) + (R)-(2,2-dimethyl-1,3-dioxolan-4-yl)acetylene (186521-82-4) → (3R,4S)-4-(4-(benzyloxy)phenyl)-3-((4'R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-(4-fluorophenyl)azetidin-2-one (1240816-36-7)

Guidance literature:

(R)-(2,2-dimethyl-1,3-dioxolan-4-yl)acetylene; With triethylamine; copper(l) iodide; In acetonitrile; at 0 ℃; for 0.333333h; Inert atmosphere;

(Z)-N-(4-(benzyloxy)benzylidene)-4-fluoroaniline-N-oxide; In acetonitrile; for 24h; Inert atmosphere;

Reference yield: 41.0%

N-(4-fluorophenyl)-α-(4-benzyloxyphenyl)nitrone (1240815-99-9) + (R)-(2,2-dimethyl-1,3-dioxolan-4-yl)acetylene (186521-82-4) → (3R,4S)-4-(4-(benzyloxy)phenyl)-3-((4'R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-(4-fluorophenyl)azetidin-2-one (1240816-36-7) + C27H26FNO4 (1316784-95-8) + C27H26FNO4 (1316784-92-5) + C27H26FNO4 (1316784-90-3)

Guidance literature:

(R)-(2,2-dimethyl-1,3-dioxolan-4-yl)acetylene; With copper(l) iodide; N,N,N',N'-tetramethylguanidine; In acetonitrile; at 0 ℃; Inert atmosphere;

N-(4-fluorophenyl)-α-(4-benzyloxyphenyl)nitrone; In acetonitrile; at 20 ℃; for 16h; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/jo2010846

Reference yield:

4-fluoro-N-hydroxyaniline (406-00-8) → (3R,4S)-4-(4-(benzyloxy)phenyl)-3-((4'R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-(4-fluorophenyl)azetidin-2-one (1240816-36-7) + C27H26FNO4 (1316784-95-8) + C27H26FNO4 (1316784-92-5) + C27H26FNO4 (1316784-90-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: methanesulfonic acid / acetone / 2 h / 20 °C

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

2.2: 16 h / 20 °C / Inert atmosphere

With copper(l) iodide; methanesulfonic acid; N,N,N',N'-tetramethylguanidine; In acetone; acetonitrile; 2.2: Kinugasa reaction;

DOI:10.1021/jo2010846

upstream raw materials:

(Z)-N-(4-(benzyloxy)benzylidene)-4-fluoroaniline-N-oxide

(R)-(2,2-dimethyl-1,3-dioxolan-4-yl)acetylene

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

4-fluoro-N-hydroxyaniline

Downstream raw materials:

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

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

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