168418-31-3

Basic information

• Product Name: p-methoxybenzyl (E)-3,4-dichloro-2-<2-oxo-3-(phenylacetamido)-4-<(phenylsulfonyl)thio>azetidin-1-yl>-2-butenoate
• Synonyms: p-methoxybenzyl (E)-3,4-dichloro-2-<2-oxo-3-(phenylacetamido)-4-<(phenylsulfonyl)thio>azetidin-1-yl>-2-butenoate
• CAS NO: 168418-31-3
• Molecular Weight: 649.573
• Mol File: 168418-31-3.mol

Chemical Properties

• CAS DataBase Reference: p-methoxybenzyl (E)-3,4-dichloro-2-<2-oxo-3-(phenylacetamido)-4-<(phenylsulfonyl)thio>azetidin-1-yl>-2-butenoate(CAS DataBase Reference)
• NIST Chemistry Reference: p-methoxybenzyl (E)-3,4-dichloro-2-<2-oxo-3-(phenylacetamido)-4-<(phenylsulfonyl)thio>azetidin-1-yl>-2-butenoate(168418-31-3)
• EPA Substance Registry System: p-methoxybenzyl (E)-3,4-dichloro-2-<2-oxo-3-(phenylacetamido)-4-<(phenylsulfonyl)thio>azetidin-1-yl>-2-butenoate(168418-31-3)

Safety Data

• Hazardous Substances Data: 168418-31-3(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 
• 168418-30-2 p-methoxybenzyl (E)-3-chloro-2-<2-oxo-3-(phenylacetamido)-4-<(phenylsulfonyl)thio>azetidin-1-yl>-4-<<(trifluoromethyl)sulfonyl>oxy>-2-butenoate 

Downstream Products

• 190790-85-3 (7R,8R)-7-phenylacetamido-3-[propen-1-yl]-3-cephem-4-carboxylic acid p-methoxybenzyl ester 
• 131111-05-2 (6R,7R)-3-(2-Methyl-propenyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl 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 
• 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 
• 119608-90-1 7-(phenylacetyl)amino-3-vinyl-4-cephalosporanic acid p-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 

Relevant articles and documents

Synthesis of 2-exo-Methylenepennam by Reductive 1,2-Elimination and S-S Bond Fission in a PbBr2/Al Bimetal System

A convenient synthesis of 2-exo-methylenepenam was performed by reductive elimination of 3,4-disubstituted chlorine atom(s) and/or a triflate moiety and S-S bond fission of the phenylsulfonylthio group of p-methoxybenzyl 3,4-dichloro or 4-chloro-3-(triflu

Construction of cephem framework via sequential reductive 1,2-elimination-hydride addition in a tributyltin hydride-copper(I) chloride-NMP system: Synthesis of 3-norcephalosporin

A sequential reductive 1,2-elimination and hydride addition process for 3,4-disubstituted butenoates derived from penicillin is successfully performed with the aid of a combination of tributyltin hydride and copper(I) chloride in N-methyl-2-pyrrolidinone

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.