124156-22-5

Usage

Chemical compound

2-Azetidinecarboxylic acid, 3-ethenyl-1-(4-methoxyphenyl)-4-oxo-, methyl ester, (2R,3R)-rel-

Stereoisomer

(2R,3R)-rel-

Derivative

Methyl ester

Groups present

Azetidine, carboxylic acid, ethenyl, 4-methoxyphenyl

Chirality

Chiral molecule

Applications

Pharmaceuticals, organic synthesis, material science

Potential uses

Further research into properties and uses may be warranted

Upstream product

• 3066-75-9 allyl diethyl phosphate 
• 201230-82-2 carbon monoxide 
• 203252-06-6 methyl (E)-2-((4-methoxyphenyl)imino)acetate 
• 625-35-4 trans-chrotonyl chloride 
• 124156-20-3 (4-methoxyphenyl-benzylidene)-carbamic acid methyl ester 
• 104-94-9 4-methoxy-aniline 

Downstream Products

• 112114-01-9 1-p-anisyl-3-ethyl-4-acetoxy-2-azetidinone 
• 124223-53-6 cis-1-p-anisyl-3-ethyl-4-carboxy-2-azetidinone 
• 124156-23-6 cis-3-Ethyl-4-(methoxycarbonyl)-1-(4-methoxyphenyl)azetidin-2-one 
• 124156-30-5 Z-3-Ethylidene-4-(methoxycarbonyl)-1-(4-methoxyphenyl)azetidin-2-one 

Relevant academic research and scientific papers

Intramolecular opening of β-lactams with amines as a strategy toward enzymatically or photochemically triggered activation of lactenediyne prodrugs

In order to develop a general strategy for selective activation of designed enediyne prodrugs belonging to the "lactenediyne" family, we studied the scope of intramolecular transamidation of simple monocyclic β-lactams bearing a tethered amine. The effect of substituents, of reaction media, and of the type of tether, on the rate of transamidation is disclosed. The possibility of triggering the transamidation event under mild conditions by the action of suitable enzymes or UV light was demonstrated on model monocyclic β-lactams. Finally, the strategy of intramolecular opening of the β-lactam leading to a larger seven-membered ring was employed on a lactenediyne, demonstrating that ring enlargement could unleash the reactivity of the enediyne moiety. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Palladium-Catalyzed Carbonylative Cycloaddition for the Stereoselective Synthesis of Either cis- or trans-3-Alkenyl β-Lactams

A new potential alkenylketene equivalent, prepared without use of a carboxylic acid or an activated derivative, has been exploited.Palladium-catalyzed carbonylation of an allyl phosphate in the presence of an imine and a tertiary amine under CO pressure (

β-Lactams via α,β-Unsaturated Acid Chlorides: Intermediates for Carbapenem Antibiotics

Stereocontrolled synthesis of α-vinyl β-lactams and their transformation to convenient intermediates for PS-5, PS-6, asparenomycin, and thienamycin are described.