383186-38-7

Basic information

• Product Name: 2-Azetidinone, 3-[(1R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-4-(phenylsulfonyl)-, (3S,4R)-
• CAS NO: 383186-38-7
• Molecular Formula: C17H27NO4SSi
• Molecular Weight: 369.557
• Mol File: 383186-38-7.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 2-Azetidinone, 3-[(1R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-4-(phenylsulfonyl)-, (3S,4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azetidinone, 3-[(1R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-4-(phenylsulfonyl)-, (3S,4R)-(383186-38-7)
• EPA Substance Registry System: 2-Azetidinone, 3-[(1R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-4-(phenylsulfonyl)-, (3S,4R)-(383186-38-7)

Safety Data

• Hazardous Substances Data: 383186-38-7(Hazardous Substances Data)

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 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 
• 81902-61-6 <3S-<3α(S^*),4β>>-t-butyl 1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone-4-carboxylate 
• 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 
• 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 
• 123994-10-5 (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 methyl ester 
• 123994-10-5 (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 methyl ester 
• 76431-32-8 methyl 6α-bromo,6β-1'-(R)-hydroxyethyl penicillanate 
• 74189-21-2 (2S,6R)-6-((R)-1-Hydroxy-ethyl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester 
• 105397-25-9 (3S,4R)-4-(Methylsulfonyl)-3-<(R)-1-(tert-butyldimethylsiloxy)ethyl>-1-(1-(methoxycarbonyl)-2-methyl-1-propenyl)-2-azetidinone 
• 82008-55-7 <3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-acetyl-2-azetidinone 
• 81902-55-8 <3S-<3α(S^*),4α>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-acetyl-2-azetidinone 
• 81902-56-9 <3S-<3α(S^*),4α>>-3-(1-t-butyldimethylsilyloxyethyl)-4-acetyl-2-azetidinone 

Downstream Products

• 84362-41-4 (3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-(p-tolylsulfonyloxymethyl)-2-azetidinone 
• 85254-01-9 (2R,6S)-6-((R)-1-Hydroxy-ethyl)-7-oxo-3-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester 
• 85253-99-2 p-nitrobenzyl 2-<(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-iodomethyl-2-oxo-1-azetidinyl>-2-chloroacetate 
• 85253-98-1 p-nitrobenzyl 2-<(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-iodomethyl-2-oxo-1-azetidinyl>-2-hydroxyacetate 
• 85254-00-8 (2S,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-7-oxo-3-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester 
• 85254-00-8 (2R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-7-oxo-3-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester 
• 1339193-55-3 (3S,4R)-3-[(1R)-1-(tert-butyldimethylsilanyloxy)ethyl]-1-(methylthio)-4-(phenylsulfonyl)azetidin-2-one 

Relevant articles and documents

Antibacterial Agents and Cystic Fibrosis: Synthesis and Antimicrobial Evaluation of a Series of N-Thiomethylazetidinones

The increasing emergence of multidrug-resistant microorganisms is one of the greatest challenges in the clinical management of infectious disease. New antimicrobial agents are therefore urgently required, particularly in the treatment of chronic and recurrent infections often associated with antibiotic-resistant pathogens, as in the case of cystic fibrosis (CF) patients. This study reports the antibacterial activity of a series of monocyclic β-lactams with an alkylidenecarboxyl chain or electron-withdrawing groups such as 4-OAc, 4-SAc, and 4-SO2Ph at the C4 position of the ring. N-Unsubstituted and N-thiomethyl derivatives were compared. A total of 33 azetidinones were tested for their activity against Gram-positive and Gram-negative bacterial clinical isolates. The combination of an N-thiomethyl group and a benzyl ester on the 4-alkylidene side chain were found to increase the potency against Gram-positive bacteria. The N-thiomethyl group clearly elevated the activity of 4-acetoxyazetidinones relative to the corresponding NH derivatives. The most active compounds showed minimum inhibitory concentration (MIC) values of 4 and 8mgL-1 against methicillin-resistant Staphylococcus aureus isolated from pediatric patients with CF.

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.