218782-74-2

Basic information

• Product Name: (+/-)-1-(O-benzyl)-4-((2-phenyl)ethyl)-2-azetidinone
• Synonyms: (+/-)-1-(O-benzyl)-4-((2-phenyl)ethyl)-2-azetidinone
• CAS NO: 218782-74-2
• Molecular Weight: 281.354
• Mol File: 218782-74-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (+/-)-1-(O-benzyl)-4-((2-phenyl)ethyl)-2-azetidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-1-(O-benzyl)-4-((2-phenyl)ethyl)-2-azetidinone(218782-74-2)
• EPA Substance Registry System: (+/-)-1-(O-benzyl)-4-((2-phenyl)ethyl)-2-azetidinone(218782-74-2)

Safety Data

• Hazardous Substances Data: 218782-74-2(Hazardous Substances Data)

Upstream product

• 622-33-3 N-benzyloxyamine 
• 183245-66-1 (+/-)-4-(2-phenylethyl)oxetan-2-one 
• 104-53-0 3-phenyl-propionaldehyde 
• 55628-83-6 1-(1H-imidazol-1-yl)-3-phenylpropan-1-one 
• 501-52-0 3-Phenylpropionic acid 
• 2687-43-6 O-benzylhydoxylamine hydrochloride 
• 129880-16-6 3-hydroxy-5-phenyl-pentanoic acid methyl ester 
• 30414-58-5 methyl 3-oxo-5-phenylpentanoate 
• 218782-73-1 3-Hydroxy-5-phenyl-pentanoic acid benzyloxy-amide 

Downstream Products

• 218782-99-1 2-Oxo-4-phenethyl-azetidine-1-carboxylic acid tert-butyl ester 
• 444023-50-1 3-benzyl-4-phenethyl-oxazolidine-2,5-dione 
• 444023-46-5 (+/-)-1-benzyl-3-oxo-4-(phenethyl)-2-azetidinone 
• 147526-02-1 (+/-)-4-(2-phenylethyl)-2-azetidinone 

Relevant articles and documents

Enantioselective synthesis of α-amino acids from N-tosyloxy β-lactams derived from β-keto esters

A novel synthetic sequence has been developed to convert simple β-keto esters into enantiomerically enriched α-amino acids. The key features of this sequence include the addition of azide to the C3 position of β-keto ester derived N-tosyloxy-β-lactams through a concomitant nucleophilic addition/N-O bond reduction reaction, a mild CsF-induced N1 benzylation of α-azido monocyclic β-lactams, the preparation of α-keto-β-lactams through a novel four-step sequence from the corresponding 3-azido-1-benzyl-β-lactams, and TEMPO-mediated ring expansion of these compounds to the corresponding N-carboxy anhydrides (NCAs). In addition, the synthesis, isolation, and characterization of unusual 3-imino and 3-chloramino-β-lactams is reported.

Total synthesis and immunosuppressive activity of (-)-pateamine A and related compounds: Implementation of a β-lactam-based macrocyclization

The asymmetric synthesis of the potent immunosuppressive agent (-)- pateamine A isolated from the marine sponge Mycale sp. is described. A key strategy employed in the synthesis was a β-lactam-based macrocyclization to form the 19-membered dilactone macrolide. The synthesis confirms the relative and absolute stereochemistry as 3R,5S, 10S,24S and sets the stage for studies into the mechanism of action of pateamine A. Other studies and findings made in the course of the synthesis and described herein include the following: (1) a Stille coupling can be competitive with π-allyl formation, (2) SmI2 effects a mild N-O cleavage of N-benzyloxy-β-lactams, (3) the synthesis of a pateamine A-dexamethasone hybrid molecule for use in a yeast three-hybrid assay was accomplished, and (4) IC50 values were determined for synthetic and natural pateamine A and related compounds in the interleukin 2 reporter gene assay.