183194-06-1

Basic information

• Product Name: p-methoxybenzyl (Z)-3-chloro-4-{[(p-methylphenyl)sulfonyl]oxy}-2-{2-oxo-3-(phenylacetamido)-4-[(phenylsulfonyl)thio]azetidin-1-yl}-2-butenoate
• Synonyms: p-methoxybenzyl (Z)-3-chloro-4-{[(p-methylphenyl)sulfonyl]oxy}-2-{2-oxo-3-(phenylacetamido)-4-[(phenylsulfonyl)thio]azetidin-1-yl}-2-butenoate
• CAS NO: 183194-06-1
• Molecular Weight: 785.316
• Mol File: 183194-06-1.mol

Chemical Properties

• CAS DataBase Reference: p-methoxybenzyl (Z)-3-chloro-4-{[(p-methylphenyl)sulfonyl]oxy}-2-{2-oxo-3-(phenylacetamido)-4-[(phenylsulfonyl)thio]azetidin-1-yl}-2-butenoate(CAS DataBase Reference)
• NIST Chemistry Reference: p-methoxybenzyl (Z)-3-chloro-4-{[(p-methylphenyl)sulfonyl]oxy}-2-{2-oxo-3-(phenylacetamido)-4-[(phenylsulfonyl)thio]azetidin-1-yl}-2-butenoate(183194-06-1)
• EPA Substance Registry System: p-methoxybenzyl (Z)-3-chloro-4-{[(p-methylphenyl)sulfonyl]oxy}-2-{2-oxo-3-(phenylacetamido)-4-[(phenylsulfonyl)thio]azetidin-1-yl}-2-butenoate(183194-06-1)

Safety Data

• Hazardous Substances Data: 183194-06-1(Hazardous Substances Data)

Upstream product

• 131857-34-6 (E)-2-((2R,3R)-2-Benzenesulfonylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-4-chloro-3-hydroxy-but-2-enoic acid 4-methoxy-benzyl ester 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 139501-51-2 3-chloro-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxybenzyl ester 
• 139371-98-5 3-methylene-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-methoxybenzyl ester 
• 189315-24-0 8-oxo-7-phenylacetylamino-3-(toluene-4-sulfonyloxy)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxybenzyl ester 
• 139472-60-9 2-((2R,3R)-2-Benzenesulfonylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-buta-2,3-dienoic acid 4-methoxy-benzyl ester 

Relevant articles and documents

Synthesis of 2-exo-methylenepenam and 3-chloro-Δ3-cephem through a sequential reductive 1,2-elimination/S-S bond fission or chloride ion-addition/cyclization of 3,4-disubstituted 2-butenoates in metal salt/metal combinations

Synthesis of 2-exo-methylenepenam 1 through a sequential reductive 1,2-elimination/S-S bond fission/cyclization of 6 was performed by treatment with a PbBr2/Al (or a BiCl3/Al) combination in DMF, while that of 3-chloro-Δ3-cephem 2 through reductive 1,2-elimination/chloride ion-addition/cyclization was attained by use of an AlCl3/Al combination in N-methylpyrrolidone (NMP). The selective transformation of 6 to the allenecarboxylate 3 was also achieved by treatment with an AlBr3/Al combination in NMP. Cyclic voltammograms of 3,4-disubstituted 2-[2-oxo-3-(phenylacetamido)-4-[(phenylsulfonyl)thio]azetidin-1-yl]-2- butenoates (6) exhibit two irreversible reduction peaks responsible for reductive 1,2-elimination of the 3,4-disubstituted 2-butenoate moiety (at less negative potential) and for reductive S-S bond fission of the (phenylsulfonyl)thio moiety, suggesting that the reductive 1,2-elimination of 6 leading to allenecarboxylate 3 would occur prior to the reductive S-S bond cleavage.