135299-72-8

Upstream product

• 107550-89-0 4-(diphenylmethoxycarbonyl)-7β-phenylacetamidoceph-3-en-3-ylmethylphosphonium iodide 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 122553-60-0 (6R,7R)-benzhydryl 8-oxo-7-(2-phenylacetamido)-3-(((trifluoromethyl)sulfonyl)oxy)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 
• 100-52-7 benzaldehyde 
• 91439-21-3 cephalosporin 3'-triphenylphosphonium ylide 

Relevant academic research and scientific papers

Reductive cross-coupling of 3-substituted Δ3-cephems with alkenyl halides in an Al/PbBr2/NiBr2(bpy) triplemetal redox system. Synthesis of 3-alkenyl-Δ3-cephems

Synthesis of 3-alkenyl-Δ3-cephems was performed successfully by cross-coupling 3-(trifluoromethylsulfonyloxy or chloro)-Δ3-cephem with alkenyl halides, e.g., vihyl bromide, trans-1-bromo-1-propene, and trans-β-bromostyrene in an Al/cat·PbBr2/cat·NiBr2(bpy)/NMP (or DMF) system. Reduction of 3-(trifluoromethylsulfonyloxy)-Δ3-cephem into norcephalosporin was also achieved by a similar reaction in the presence of 5 molar equiv of water. Scope and a plausible mechanism of the Al/Pb/Ni triplemetal-redox promoted reactions are discussed.

The Regioselectivity of Cycloaddition Reactions Between Diazomethane and 3-Vinylcephalosporins

Diphenylmethyl (6R,7R)-7-phenylacetamido-3-vinylceph-3-em-4-carboxylate 1 undergoes regioselective addition of diazomethane to give the 1-pyrazoline 7, which readily undergoes thermolysis of give the cyclopropyl analogue 10.The regioselectivity is reversed, however, when one or more electron withdrawing ester substituents are attached to the 3-vinyl group.