76227-80-0

Upstream product

• 76227-79-7 2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-t-butyl acetate 
• 76227-84-4 2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-mono-t-butyl malonate 
• 54275-92-2 6-β-phenylacetamidopenicillanic acid-(1S)-oxide 
• 87996-76-7 2-((1R,5R)-3-Benzyl-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-methyl-but-2-enoic acid benzyl ester 
• 87035-97-0 2-((2R,3R)-2-Mercapto-4-oxo-3-phenylacetylamino-azetidin-1-yl)-malonic acid tert-butyl ester 4-nitro-benzyl ester 
• 78833-85-9 2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-t-butyl and p-nitrobenzyl malonate 
• 34103-69-0 (1E,5R)-3-Phenylmethyl-4-thia-2,6-diazabicyclo[3.2.0]hept-2-en-7-one 
• 69-57-8 Penicillin G sodium 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 87035-90-3 (5R,6R)-3,7-Dioxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2,2-dicarboxylic acid tert-butyl ester 4-nitro-benzyl ester 
• 76227-87-7 2-((2R,3R)-2-Mercapto-4-oxo-3-phenylacetylamino-azetidin-1-yl)-malonic acid mono-tert-butyl ester 

Downstream Products

• 76227-81-1 (6R)-phenylacetamido-2-methoxy-(5R)-penem-3-t-butyl-carboxylate 
• 78815-29-9 (6R)-phenylacetamido-2-benzoyloxy-(5R)-penem-3-t-butyl-carboxylate 

Relevant academic research and scientific papers

Synthesis of 2-oxo-penams and penems from penicillin G

Using Penicillin G as starting material, general methods of synthesis for the 2-oxo-penam skeleton have been established. Compounds 7 represent a new group of strained penicillin derivatives. They can be readily transformed into 2-alkoxy 17 or benzoyloxypenems 18.

A GENERAL ROUTE TOWARD 2-OXO-, 2-THIOXO- AND 2-IMINOPENAMS AND THEIR CONVERSION INTO 2-ALKOXY-, 2-ALKYLTHIO- AND 2-AMINOPENEMS

A convenient methodology is described which allows the preparation of 2-oxo-, 2-thioxo- and 2-iminopenams from a single precursor readily prepared from penicillin G.These penams have been converted into the corresponding 2-heterosubstituted penems.