121406-67-5

Upstream product

• 10209-10-6 diphenylmethyl (6R,7R)-3-methyl-7β-phenoxyacetamidoceph-3-em-4-carboxylate 
• 107-13-1 acrylonitrile 
• 134930-73-7 diphenylmethyl (1S,6R,7R)-4-(2'-cyanoethyl)-3-methyl-7β-phenoxyacetamidoceph-2-em-4-carboxylate 1-oxide 
• 121406-69-7 2-(2-Cyano-ethyl)-3-methyl-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid benzhydryl ester 

Downstream Products

• 134930-73-7 diphenylmethyl (1S,6R,7R)-4-(2'-cyanoethyl)-3-methyl-7β-phenoxyacetamidoceph-2-em-4-carboxylate 1-oxide 
• 134847-02-2 diphenylmethyl (6R,7R)-4-(2'-cyanoethyl)-3-methyl-7β-phenoxyacetamidoceph-2-em-4-carboxylate 1,1-dioxide 
• 134830-19-6 (6R,7R)-4-(2'-cyanoethyl)-3-methyl-7β-phenoxyacetamidoceph-3-em 1,1-dioxide 
• 134830-16-3 (1S,6R,7R)-4-(2'-cyanoethyl)-3-methyl-7β-phenoxyacetamidoceph-3-em 1-oxide 
• 134830-20-9 (6R,7R)-4-(2'-cyanoethyl)-3-methyl-7β-phenoxyacetamidoceph-3-em 

Relevant academic research and scientific papers

Chemistry of Cephems: C-4 Substitution and Sulphoxide De-oxygenation Reactions.

The anion derived from ceph-3-em esters adds readily to Michael acceptors to give C-4 disubstituted ceph-2-ems.Oxidation of a typical adduct, such as the 4-cyanoethyl-4-diphenylmethyl ester, followed by ester hydrolysis and decarboxylation, gives the 4-cyanoethylceph-3-em sulphoxide which is easily reduced to the sulphide.Furthermore, zinc-acetic acid in DMF (dimethylformamide) is found to be an effective, mild reagent for the de-oxygenation of ceph-2-em sulphoxides.

NEW METHODOLOGY FOR C-4 SUBSTITUTION AND SULPHOXIDE DE-OXYGENATION REACTIONS IN CEPH-3-EMS

Addition of Michael acceptors to the C-4 position in ceph-3-ems followed by oxidation, de-esterification, and de-carboxylation results in the formation of new 4-monosubstituted ceph-3-ems; an unusually mild de-oxygenation process for ceph-2-em sulphoxides is also described.