418080
Pentafluorophenyl diphenylphosphinate
Sinónimos:
FDPP, Diphenylphosphinic acid pentafluorophenyl ester
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About This Item
Fórmula lineal:
(C6H5)2P(O)OC6F5
Número de CAS:
Peso molecular:
384.24
Número MDL:
Código UNSPSC:
12352101
ID de la sustancia en PubChem:
NACRES:
NA.22
Productos recomendados
Formulario
solid
Nivel de calidad
mp
47-50 °C (lit.)
grupo funcional
fluoro
cadena SMILES
Fc1c(F)c(F)c(OP(=O)(c2ccccc2)c3ccccc3)c(F)c1F
InChI
1S/C18H10F5O2P/c19-13-14(20)16(22)18(17(23)15(13)21)25-26(24,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H
Clave InChI
OOWSDKUFKGVADH-UHFFFAOYSA-N
Descripción general
Pentafluorophenyl diphenylphosphinate (FDPP) is a reagent, used as a coupling agent in the amide bond forming reactions without racemization. It can also be employed in the synthesis of dipeptides with high yields and good optical purity. FDPP can be prepared from diphenylphosphinic chloride and pentafluorophenol in the presence of imidazole.
Aplicación
Catalyst involved in coupling and macrocyclization
Reagent used in:
Reagent used in:
- Fmoc solid-phase synthesis
- Synthesis of phorboxazoles, furan-based cyclic homoligopeptides, and ziziphine N
FDPP can be used as a coupling reagent in the:
- Synthesis of peptides by solid-phase and solution-phase reactions.
- Preparation of macrocyclic peptide cyclotheonamide B as a thrombin inhibitor.
- Cyclooligomerization of N-methylated-L-valine thiazole amino acid to obtain its cyclic tetramers.
- Macrocyclization of an intermediate for the total synthesis of ziziphine N , and for the macrolactamization of precursor in synthesizing cryptophycin D.
Código de clase de almacenamiento
11 - Combustible Solids
Clase de riesgo para el agua (WGK)
WGK 3
Punto de inflamabilidad (°F)
Not applicable
Punto de inflamabilidad (°C)
Not applicable
Equipo de protección personal
Eyeshields, Gloves, type N95 (US)
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Highly convergent route to cyclopeptide alkaloids. Total synthesis of ziziphine N.
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Synthesis of novel N-methylated thiazole-based cyclic octa-and dodecapeptides.
Dudin L, et al.
Tetrahedron, 61(5), 1257-1267 (2005)
Total synthesis of cryptophycins. Revision of the structures of cryptophycins A and C.
Barrow R A, et al.
Journal of the American Chemical Society, 117(9), 2479-2490 (1995)
Pentafluorophenyl diphenylphosphinate a new efficient coupling reagent in peptide chemistry.
Chen S and Xu J
Tetrahedron Letters, 32(46), 6711-6714 (1991)
Gang He et al.
Organic letters, 9(7), 1367-1369 (2007-03-10)
[structure: see text]. A highly convergent protocol to cyclopeptide alkaloids, as demonstrated by the first total synthesis of antiplasmodial agent ziziphine N, is developed. The key elements include construction of its aryl ether unit via Mitsunobu reaction, installation of its
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