74481-22-4

Basic information

• Product Name: benzyl (2S,5R)-6,6-bis(phenylseleno)penicillanate
• Synonyms: benzyl (2S,5R)-6,6-bis(phenylseleno)penicillanate
• CAS NO: 74481-22-4
• Molecular Weight: 601.486
• Mol File: 74481-22-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: benzyl (2S,5R)-6,6-bis(phenylseleno)penicillanate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl (2S,5R)-6,6-bis(phenylseleno)penicillanate(74481-22-4)
• EPA Substance Registry System: benzyl (2S,5R)-6,6-bis(phenylseleno)penicillanate(74481-22-4)

Safety Data

• Hazardous Substances Data: 74481-22-4(Hazardous Substances Data)

Upstream product

• 1666-13-3 diphenyl diselenide 
• 15058-70-5 benzyl (2S)-6-diazo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 
• 15058-70-5 6-diazopenicillanic acid benzyl ester 
• 645-96-5 Benzeneselenol 
• 1254-56-4 benzyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 
• 50269-19-7 C₂₃H₂₃N₃O₅S 

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 
• 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 
• 85253-94-7 benzyl 2-<(3S,4R)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-methylsulfonyl-2-oxo-1-azetidinyl>-3-methyl-2-butenoate 
• 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 
• 85253-93-6 (2S,5R,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 
• 83204-40-4 benzyl (2S,5R,6R)-6-<(R)-1-(t-butyldimethylsilyloxy)ethyl>penicillanate 1,1-dioxide 
• 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 
• 62263-79-0 benzyl (2S,5R,6R)-6-<(R)-1-hydroxyethyl>penicillanate 
• 83212-60-6 benzyl (2S,5R,6S)-6-<(R)-1-hydroxyethyl>-6-(phenylseleno)penicillanate 
• 74481-23-5 benzyl (2S,5R,6R)-6-(phenylseleno)penicillanate 
• 74481-12-2 (2S,6R)-3,3-Dimethyl-7-oxo-6-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 
• 83162-13-4 (2S,6R)-6-((S)-1-Hydroxy-ethyl)-3,3-dimethyl-7-oxo-6-phenylselanyl-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 

Relevant articles and documents

From penicillin to penem and carbapenem. IX. C1-unit introduction and the carbapenam synthesis from the penicillin molecule

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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.