124242-54-2

Upstream product

• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 104-94-9 4-methoxy-aniline 
• 124156-35-0 1-p-anisyl-3-isopropylidene-4-carbethoxy-2-azetidinone 
• 124156-25-8 cis-1-p-Methoxyphenyl-3-isopropenyl-4-ethoxycarbonylazetidinone 
• 119873-85-7 cis-1-p-Methoxyphenyl-3-vinyl-4-ethoxycarbonylazetidinone 
• 124156-32-7 3-Eth-(E)-ylidene-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid ethyl ester 
• 124156-21-4 ethyl (4-methoxyphenylimino)acetate 
• 124156-36-1 1-p-anisyl-3-isopropylidene-4-carboxy-2-azetidinone 
• 546-67-8 lead(IV) tetraacetate 

Relevant academic research and scientific papers

Transformation of 4-acetoxy-3-vinylazetidin-2-ones to 3-(1-hydroxyethyl)azetidin-2-ones and 3-ethylideneazetidin-2-ones intermediates for carbapenem antibiotics

4-acetoxy-3-vinylazetidin-2-one and 4-acetoxy-3-isopropenylazetidin-2-one were transformed to the carbapenem intermediates 4-acethoxy-3-(1-hydroxyethyl)azetidin-2-ones and 4-acethoxy-3-[2-(2-hydroxypropyl)]-4-acetoxyazetidin-2-ones respectively by a sequence of direct bromohydrin formation followed by reductive debromination. Transformation of 4-formyl-3-vinylazetidin-2-ones to 4-acetoxy-3-ethylideneazetidin-2-ones was also carried out. We have also demonstrated the synthesis of a 6-vinylcarbapenem.

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.