78385-39-4

Upstream product

• 78385-35-0 benzyloxycarbonylbromomethylenetriphenylphosphorane 
• 78385-37-2 benzyl 2-bromocyclopropylideneacetate 
• 61534-76-7 (3R,4R)-4-mercapto-3-phenoxyacetamidoazetidin-2-one 
• 78385-38-3 1-<(2R,3R)-4-oxo-3-phenoxyacetamidoazetidin-2-ylthio>-1-(1-benzyloxycarbonyl-1-bromomethyl)cyclopropane 

Downstream Products

• 78385-41-8 (3S,5R,6R)-6-phenoxyacetamidocyclopropanespiro-2-bisnorpenicillanic acid 
• 78385-34-9 (3S,5R,6R)-benzyl 6-aminocyclopropanespiro-2-bisnorpenicillanate 
• 78385-43-0 (3S,5R,6R)-benzyl 6-D-α-aminophenylacetamidocyclopropanespiro-2-bisnorpenicillanate 
• 78385-30-5 (3S,5R,6R)-6-D-α-aminophenylacetamidocyclopropanespiro-2-bisnorpenicillanic acid 

Relevant academic research and scientific papers

The Chemistry of 4-Mercaptoazetidin-2-ones. Part 4. Synthesis of Cyclopropanespiro-2-bisnorpenicillanic Acids

Reaction of the 4-mercaptoazetidin-2-one (6) with benzyl 2-bromocyclopropylideneacetate (7) gave the C-3 epimeric cyclopropanespiro-2-bisnorpenicillanates (9) and (10).Standard procedures were used to convert the 3S-epimer into the ampicillin analogue (15).Hydrogenolysis of the esters (9) and (15) gave the cyclopropanespiro-2-bisnorpenicillanic acids (13) and (16) both of which had antibacterial properties similar to those of the corresponding penicillins.