20425-27-8

Basic information

• Product Name: (2S,5R,6R)-6-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• CAS NO: 20425-27-8
• Molecular Formula: C₁₆H₁₄N₂O₅S
• Molecular Weight: 346.3578
• Mol File: 20425-27-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 605.7°C at 760 mmHg
• Flash Point: 320.1°C
• Density: 1.63g/cm³
• Vapor Pressure: 1.6E-15mmHg at 25°C
• Refractive Index: 1.731
• CAS DataBase Reference: (2S,5R,6R)-6-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5R,6R)-6-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid(20425-27-8)
• EPA Substance Registry System: (2S,5R,6R)-6-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid(20425-27-8)

Safety Data

• Hazardous Substances Data: 20425-27-8(Hazardous Substances Data)

Upstream product

• 551-16-6 6-Aminopenicillanic Acid 
• 22509-74-6 N-ethoxycarbonylphthalimide 
• 87-53-6 penicillanic acid 
• 19788-65-9 methyl (3S,5R,6R)-6-phthalimidopenicillanate 
• 40124-92-3 6R(β)-tritylaminopenicillanic acid 

Downstream Products

• 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 
• 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 
• 65102-83-2 benzyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-phthalisoimido-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 
• 1316164-16-5 benzyl (2S,5R,6S)-6-[(N-decanoyl-L-prolyl-L-threonyl-L-alanyl-L-asparaginyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]-heptane-2-carboxylate 
• 1316164-14-3 benzyl (2S,5R,6R)-6-[(N-decanoyl-L-prolyl-L-threonyl-L-alanyl-L-asparaginyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]-heptane-2-carboxylate 
• 1316164-07-4 benzyl (2S,5R,6S)-3,3-dimethyl-7-oxo-6-phthalisoimido-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 
• 1316164-02-9 2-[(2S,5R,6S)-2-(benzyloxycarbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-6-ylcarbamoyl]benzoic acid 
• 49626-54-2 benzyl (2S,5R,6S)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 
• 3956-31-8 benzyl (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 
• 65102-82-1 2-[(2S,5R,6R)-2-(benzyloxycarbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-6-ylcarbamoyl]benzoic acid 
• 551-16-6 6-Aminopenicillanic Acid 
• 95320-04-0 ((5R)-3,3-dimethyl-7-oxo-6t-phthalimido-(5rH)-4-thia-1-aza-bicyclo[3.2.0]hept-2c-yl)-carbamic acid benzyl ester 
• 34706-15-5 (2S,5S,6R)-6-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 

Relevant articles and documents

Comparison of various density functional methods for distinguishing stereoisomers based on computed1H or13C NMR chemical shifts using diastereomeric penam β-lactams as a test set

Full 1H and 13C NMR chemical shift assignments were made for two sets of penam β-lactams: namely, the diastereomeric (2S,5S,6S)-, (2S,5R,6R)-, (2S,5S,6R)-, and (2S, 5R, 6S)-methyl 6-(1,3-dioxoisoindolin-2-yl)3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0] heptane-2-carboxylates (1-4) and (2S,5R,6R)-, (2S,5S,6R)-, and (2S,5R,6S)-6-(1,3-dioxoisoindolin-2-yl)-3,3-dimethyl-7-oxo-4-thia-1-aza- bicyclo[3.2.0]heptane-2carboxylic acids (6-8). Each penam was then modeled as a family of conformera obtained from Monte Carlo searches using the AMBER* force field followed by IEFPCM/B3LYP/6-31G(d) geometry optimization of each conformer using chloroform solvation. 1H and 13C chemical shifts for each conformer were computed at the WF04, WC04, B3LYP, and PBE1 density functional levels as Boltzmann averages of IEFPCM/B3LYP/6-311+G(2d,p) energies over each family. Comparisons between experimental and theoretical chemical shift data were made using the total absolute error (|Δδ|T) criterion. For the 1H shift data, all methods were sufficiently accurate to identify the proper stereoisomers. Computed 13C shifts were not always successful in identifying the correct stereoisomer, regardless of which DFT method was used. The relative ability of each theoretical approach to discriminate among stereoisomers on the basis of proton shifts was also evaluated. Copyright

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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