84028-77-3

Basic information

• Product Name: Pentanoic acid, 4-oxo-5-(triphenylphosphoranylidene)-, methyl ester
• CAS NO: 84028-77-3
• Molecular Formula: C24H23O3P
• Molecular Weight: 390.419
• Mol File: 84028-77-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Pentanoic acid, 4-oxo-5-(triphenylphosphoranylidene)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Pentanoic acid, 4-oxo-5-(triphenylphosphoranylidene)-, methyl ester(84028-77-3)
• EPA Substance Registry System: Pentanoic acid, 4-oxo-5-(triphenylphosphoranylidene)-, methyl ester(84028-77-3)

Safety Data

• Hazardous Substances Data: 84028-77-3(Hazardous Substances Data)

Upstream product

• 603-35-0 triphenylphosphine 
• 53856-93-2 methyl 5-bromo-4-oxopentanoate 
• 98749-46-3 N-<3-(Methoxycarbonyl)propionyl>-2-(triphenylphosphoranyliden)acetanilid 
• 19493-09-5 Methylenetriphenylphosphorane 
• 1490-25-1 succinic acid monomethylester chloride 
• 98749-50-9 5-(Methoxycarbonyl)-3-oxo-2-(triphenylphosphoranyliden)pentananilid 
• 64448-06-2 (N-phenyliminovinylidene)triphenylphosphorane 

Downstream Products

• 943322-80-3 C₃₃H₄₆O₁₀S 
• 701262-89-7 (E)-6-{(4R,5S)-2,2-Dimethyl-5-[(1S,2S)-2-(toluene-4-sulfonyloxy)-1-triethylsilanyloxy-4-trimethylsilanyl-but-3-ynyl]-[1,3]dioxolan-4-yl}-4-oxo-hex-5-enoic acid methyl ester 
• 701262-90-0 (E)-6-{(4R,5S)-2,2-Dimethyl-5-[(1S,2S)-2-(toluene-4-sulfonyloxy)-1-triethylsilanyloxy-but-3-ynyl]-[1,3]dioxolan-4-yl}-4-oxo-hex-5-enoic acid methyl ester 
• 943323-19-1 C₃₂H₅₀O₉SSi₂ 
• 118908-16-0 Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-((E)-5-methoxycarbonyl-3-oxo-pent-1-enyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 84028-81-9 (E)-6-(2-Hydroxy-phenyl)-4-oxo-hex-5-enoic acid methyl ester 
• 84028-79-5 (E)-methyl 4-oxo-6-phenylhex-5-enoate 
• 84028-82-0 (E)-4-Oxo-7-phenyl-oct-5-enoic acid methyl ester 

Relevant articles and documents

On the synthesis of cepacin A

Efforts directed toward a total synthesis of cepacin A is presented in full detail. The C-7, C-8, and C-9 stereogenic centers in the target molecule were derived from d-arabinose. The configuration of the allene axis was controlled at the bromoallenation step by the C-10 configuration of the precursor. An unexpected yet very interesting phenomenon was observed with the bromoallenation, where the α-isomer of the propargylic alcohol 31 was entirely resistant to the conditions that worked so well for its β-counterpart. The problem was eventually solved by careful tuning of the size of the neighboring groups based on the clue obtained from conformational analysis. The diyne moiety was incorporated into the molecular framework through a coupling of the TMS protected diyne with a proper bromoallene under the Sonogashira conditions with EtOAc as the solvent. Use of other solvents at this step led to complete failure.

Methyl 5-(Triphenylphosphoranylidene)levulinate: A Reagent for Homologation of Aldehydes to δ-Ene γ-Keto Esters

Methyl 5-(triphenylphosphoranylidene)levulinate has been synthesized and shown to condense with aldehydes to afford E δ-ene γ-keto esters in good yield.