74536-07-5

Usage

Role in Organic Synthesis

Commonly used as a building block

Reactivity

Versatile reactivity

Potential Applications

Drug discovery and development

Pharmacological Activities

Potential anti-inflammatory
Potential anti-tumor
Potential anti-viral

Scaffold for Pharmaceutical Compounds

Due to its unique structure and reactivity

Overall Value

Valuable chemical with diverse potential applications in pharmaceutical and chemical industries

Upstream product

• 100-42-5 styrene 
• 50-00-0 formaldehyd 
• 5661-55-2 4-phenylazetidin-2-one 

Downstream Products

• 145694-38-8 4-phenyl-1-propionyloxymethyl-2-azetidinone 
• 178665-42-4 1-butyryloxymethyl-4-phenyl-2-azetidinone 
• 120420-11-3 N-t-butyldimethylsilyl-3-methyl-4-phenylazetidin-2-one 
• 37088-65-6 (3R)-4-phenyl-2-azetidinone 
• 145774-23-8 (R)-1-hydroxymethyl-4-phenyl-2-azetidinone 
• 402828-07-3 (S)-1-hydroxymethyl-4-phenyl-2-azetidinone 
• 402828-05-1 (R)-1-butyryloxymethyl-4-phenyl-2-azetidinone 
• 178665-38-8 (S)-1-butyryloxymethyl-4-phenyl-2-azetidinone 

Relevant academic research and scientific papers

Chemoenzymatic preparation of fluorine-substituted β-lactam enantiomers exploiting Burkholderia cepacia lipase

Both enantiomers of fluorinated and non-fluorinated 4-phenyl-2-azetidinones are prepared in high enantiopurities (ee 99%) by a chemoenzymatic method, using a double resolution technique to N-hydroxymethylated β-lactams in the presence of Burkholderia cepa

Synthesis of 4-aryl-substituted β-lactam enantiomers by enzyme-catalyzed kinetic resolution

Enantiopure 4-phenyl- and 4-(p-tolyl)-2-azetidinones 3a, 3b, 4a and 4b (with e.e.s of ≥96%) were prepared through lipase-catalyzed asymmetric butyrylation of the primary OH group of N-hydroxymethylated β-lactams (±)-5 and (±)-6 at the (R)-stereogenic centre or by lipase-catalyzed asymmetric debutyrylation of O-butyryloxymethyl-2-azetidinones (±)-7 and (±)-8 at the (R)-stereogenic centre. The ring-opening of lactams 5a, 5b, 6b and 8a with HCl/EtOH afforded the corresponding β-amino ester enantiomers 9a, 9b, 10a and 10b with e.e.s of ≥92%.

Convenient syntheses of optically active β-lactams by enzymatic resolution

Optically active β-lactams were synthesized by lipase-catalyzed kinetic resolution using the enantioselective hydrolysis of N-acyloxymethyl β- lactams (3) in an organic solvent and the transesterification of N- hydroxymethyl β-lactams (2) with vinyl aceta