85253-93-6

Upstream product

• 74481-22-4 benzyl (2S,5R)-6,6-bis(phenylseleno)penicillanate 
• 83212-60-6 benzyl (2S,5R,6S)-6-<(R)-1-hydroxyethyl>-6-(phenylseleno)penicillanate 
• 83162-14-5 (2S,5R,6R)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 74481-12-2 benzyl (2S,5R,6S)-6-(phenylseleno)penicillanate 
• 15058-70-5 6-diazopenicillanic acid benzyl ester 
• 74481-22-4 (S)-3,3-Dimethyl-7-oxo-6,6-bis-phenylselanyl-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 
• 83162-13-4 (2S,6S)-6-((R)-1-Hydroxy-ethyl)-3,3-dimethyl-7-oxo-6-phenylselanyl-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 
• 15058-70-5 benzyl (2S)-6-diazo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 
• 62263-73-4 (2S,6R)-6-((R)-1-Hydroxy-ethyl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 
• 83204-40-4 (2S,6R)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 

Downstream Products

• 83204-40-4 (2S,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 
• 85253-94-7 benzyl 2-<(3S,4R)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-methylsulfonyl-2-oxo-1-azetidinyl>-3-methyl-2-butenoate 
• 85254-00-8 p-nitrobenzyl (2R,5S,6S)-6-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-7-oxo-3-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 85281-74-9 p-nitrobenzyl (2S,5S,6S)-6-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-7-oxo-3-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 85254-01-9 p-nitrobenzyl (2R,5S,6S)-6-<(R)-1-hydroxyethyl>-7-oxo-3-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 383186-38-7 (3S,4R)-4-benzenesulfonyl-3-((1R)-1-(tert-butyldimethylsilanyloxy)-ethyl)-azetidin-2-one 
• 85253-98-1 p-nitrobenzyl 2-<(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-iodomethyl-2-oxo-1-azetidinyl>-2-hydroxyacetate 
• 85253-99-2 p-nitrobenzyl 2-<(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-iodomethyl-2-oxo-1-azetidinyl>-2-chloroacetate 
• 84362-41-4 (3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-(p-tolylsulfonyloxymethyl)-2-azetidinone 
• 85281-73-8 (3S,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)-ethyl]-4-phenylthio-2-azetidinone 

Relevant academic research and scientific papers

FROM PENICILLIN TO PENEM AND CARBAPENEM. II. SYNTHESIS OF 3,4-DISUBSTITUTED AZETIDINONE DERIVATIVES FROM 6,6-BIS(PHENYLSELENYL)PENICILLANATE

6,6-Bis(phenylselenyl)penicillanate 2a was converted into 6-1'-(R)-hydroxyethyl substituted penicillanate 5 in high yield.Compound 5 was deselenylated to 10.Oxidation, and then the basic epimerization of cis sulfone 11 gave trans sulfone derivative 12.The trans sulfone 12 was degraded to the monocyclic β-lactams 14, 15 which are important precursors for the carbapenem synthesis.