182186-35-2

Upstream product

• 59034-26-3 (2S,5R,6R)-benzyl 6-(1,3-dioxoisoindolin-2-yl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 
• 66363-43-7 (2S,5R,6S)-benzyl 6-(1,3-dioxoisoindolin-2-yl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 
• 20425-27-8 (2S,5R,6R)-6-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 
• 182268-26-4 (2S,5S,6S)-benzyl 6-(1,3-dioxoisoindolin-2-yl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 
• 22509-74-6 N-ethoxycarbonylphthalimide 
• 551-16-6 6-Aminopenicillanic Acid 
• 214344-42-0 (R)-2-[(2S,3S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-hydroxysulfanyl-4-oxo-azetidin-1-yl]-3-methyl-but-3-enoic acid benzyl ester 
• 182268-27-5 benzyl (-)-(2S,4S,5S,6S)-3,3-dimethyl-7-oxo-6-phthalimido-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4-oxide 
• 182268-25-3 benzyl (2S)-2-[(3S,4R)-4-chloro-3-phthalimido-2-oxazetidin-1-yl]-2-(1-chlorothio-1-methylethyl)-acetate 
• 182268-32-2 benzyl (2S)-2-[(3R,4S)-4-chloro-3-phthalimido-2-oxazetidin-1-yl]-2-(1-chlorothio-1-methylethyl)-acetate 

Downstream Products

• 182268-28-6 benzyl (-)-(6S,7S)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 
• 182268-30-0 benzyl (-)-(6S,7S)-3-methyl-8-oxo-7-phenylacetamido-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 
• 182268-29-7 benzyl (-)-(6S,7S)-3-methyl-8-oxo-7-phenoxyacetamido-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 

Relevant academic research and scientific papers

PEPTIDE ANTIBIOTICS AND METHODS OF USE THEREOF

The invention features peptide antibiotic compositions and methods of using such compositions for the treatment of bacterial infections (e.g., vancomycin resistant infections).

Syntheses of (6S)-cephalosporins from 6-aminopenicillanic acid

Two practical routes to (6S,7S)-cephalosporins from 6-aminopenicillanic acid (6-APA) are described. In the first, 6-APA was converted to (2S,4S,5S,6S)-penicillin sulfoxide 49, which underwent Morin ring expansion to a protected (6S,7S)-cephem 50. In the s

Unusually stable azetidinone sulfenic acids

Sulfoxides of (2S,5S,6S)-penams rearrange upon heating in benzene or toluene to form unusually stable azetidinone sulfenic acids. A reversal of the process, the annelation of the sulfenic acids, is disfavoured due to steric congestion on the endo-face of the corresponding penam sulfoxides.

Syntheses of (6S,7S)- and (6S,7R)-deacetoxycephalosporanic acids from 6-aminopenicillanic acid

Two practical (i.e. applicable to multigram scale synthesis) approaches to (6S,7S)-cephalosporins (i.e. the enantiomers of naturally occuring cephalosporins) and the (6S)-epimers of cephalosporins from readily available (2S,5R,6R)-6-aminopenicillanic acid