85281-77-2

Upstream product

• 85270-00-4 (4R)-4-phenylthio-2-azetidinone 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 108-98-5 thiophenol 

Downstream Products

• 90497-70-4 N-[(3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-2-oxo-4-phenylsulfanyl-azetidin-3-yl]-acetamide 
• 90497-72-6 N-[(3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-methoxy-2-oxo-4-phenylsulfanyl-azetidin-3-yl]-acetamide 
• 90497-69-1 ((2R,3S)-2-Benzenesulfinyl-3-methoxy-4-oxo-azetidin-3-yl)-carbamic acid benzyl ester 
• 90581-08-1 [(3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-2-oxo-4-phenylsulfanyl-azetidin-3-yl]-carbamic acid benzyl ester 
• 90497-65-7 (3S,4R)-3-Amino-1-(tert-butyl-dimethyl-silanyl)-4-phenylsulfanyl-azetidin-2-one 
• 90497-68-0 [(3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-methoxy-2-oxo-4-phenylsulfanyl-azetidin-3-yl]-carbamic acid benzyl ester 
• 782496-97-3 N-(tert-butyldimethylsilyl)-trans-3-methyl-4-thiophenyl-2-azetidinone 
• 85281-79-4 (3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-((R)-1-hydroxy-ethyl)-4-phenylsulfanyl-azetidin-2-one 
• 85281-80-7 (3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-((S)-1-hydroxy-ethyl)-4-phenylsulfanyl-azetidin-2-one 
• 85254-18-8 (3S,4R)-3-Acetyl-1-(tert-butyl-dimethyl-silanyl)-4-phenylsulfanyl-azetidin-2-one 
• 85254-19-9 (3S,4R)-3-((R)-1-Hydroxy-ethyl)-4-phenylsulfanyl-azetidin-2-one 
• 383186-38-7 (3S,4R)-4-benzenesulfonyl-3-((1R)-1-(tert-butyldimethylsilanyloxy)-ethyl)-azetidin-2-one 
• 85281-73-8 (3S,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)-ethyl]-4-phenylthio-2-azetidinone 
• 783340-38-5 trans-3-methyl-4-thiophenyl-2-azetidinone 

Relevant academic research and scientific papers

Suppressed β-effect of silicon in 3-silylated monocyclic β-lactams: The role of antiaromaticity

[Chemical Equation Presented] The β-stabilizing effect of silicon substituent at C-3 on a C-4 cation and a radical In the 2-azetidinone systems is studied using NMR kinetics. While the β-effect Is virtually nonexistent in the case of a cation, a foiled β-effect (only a 3-fold rate enhancement) Is observed for a radical intermediate. From both the experimental and theoretical studies, It Is demonstrated that antiaromaticity Is playing the prime role In suppressing the β-stabilizing effect of silicon.

Molecular recognition in β-lactams: The crystal packing in 4-sulfonyl β-lactams

Single crystal X-ray structures of 4-phenyl sulfonyl 2-azetidinone 1, a 1:2 conglomerate of the corresponding 3-methyl (trans) and 3,3-dimethyl derivatives 2A and 2B/2C respectively and 3-acetoxymethyl 1,4-diphenyl 2-azetidinone 3 revealed interesting variation in crystal packing dictated by H-bonding and hydrophobic interactions which may be responsible for molecular recognition in β-lactams.

The efficient synthesis of chiral key intermediates for monobactam antibiotics

Chemical asymmetric syntheses of the key intermediates (4,6,8) for the synthesis of monobactam antibiotics (SQ 26776 (azthreonam, sulfazecin, and SQ 26180) are accomplished from (±)-4-phenylsulfonyl-2-azetidinone.