139472-60-9

Upstream product

• 168418-31-3 p-methoxybenzyl (E)-3,4-dichloro-2-<2-oxo-3-(phenylacetamido)-4-<(phenylsulfonyl)thio>azetidin-1-yl>-2-butenoate 
• 186527-79-7 (E)-2-((2R,3R)-2-Benzenesulfonylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-4-chloro-3-(toluene-4-sulfonyloxy)-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 
• 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 
• 183194-06-1 p-methoxybenzyl (Z)-3-chloro-4-{[(p-methylphenyl)sulfonyl]oxy}-2-{2-oxo-3-(phenylacetamido)-4-[(phenylsulfonyl)thio]azetidin-1-yl}-2-butenoate 

Downstream Products

• 139371-98-5 3-methylene-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-methoxybenzyl ester 
• 120635-31-6 (7R,8R)-7-phenylacetamido-3-[(Z)-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 
• 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 

Relevant academic research and scientific papers

Synthesis of 3-alkenyl-Δ3-cephems via sequential reductive 1,2- elimination/ addition/cyclization in an alkenyltin/copper(I) chloride/bpy system

A sequential reductive 1,2-elimination-addition-cyclization of 3,4- disubstituted butenoates derived from penicillin is performed successfully by treatment with alkenyltin, copper(I) chloride and 2,2'-bipyridine (bpy) in N- methyl-2-pyrrolidinone (NMP) to afford 3-alkenyl-Δ3-cephems.

Synthesis of 3-allyl- and 3-benzyl-Δ3-cephems through sequential reductive 1,2-elimination/addition/cyclization of 3,4-disubstituted 2- butenoates in allyl and benzyl halides/Mn/NiCl2 /AlCl3/NMP systems

One-pot synthesis of 3-allyl- and 3-benzyl-Δ3-cephems through a sequential reductive 1,2-elimination/addition/cyclization of 3, 4- disubstituted 2-[2- oxo-3-phenylacetamido-4-(phenylsulfonylthio)azetidin- 1- yl]-2-butenoates was successfully performed by treatment with allyl and benzyl halides in an Mn/NiCl2(bpy)/AlCl3/N-methyl-2-pyrroridinone (NMP) system.

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.