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Pentafluorophenyl diphenylphosphinate
Synonim(y):
FDPP, Diphenylphosphinic acid pentafluorophenyl ester
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About This Item
Wzór liniowy:
(C6H5)2P(O)OC6F5
Numer CAS:
Masa cząsteczkowa:
384.24
Numer MDL:
Kod UNSPSC:
12352101
Identyfikator substancji w PubChem:
NACRES:
NA.22
Polecane produkty
Postać
solid
Poziom jakości
mp
47-50 °C (lit.)
grupa funkcyjna
fluoro
ciąg 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
Klucz InChI
OOWSDKUFKGVADH-UHFFFAOYSA-N
Opis ogólny
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.
Zastosowanie
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.
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Kod klasy składowania
11 - Combustible Solids
Klasa zagrożenia wodnego (WGK)
WGK 3
Temperatura zapłonu (°F)
Not applicable
Temperatura zapłonu (°C)
Not applicable
Środki ochrony indywidualnej
Eyeshields, Gloves, type N95 (US)
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Journal of the American Chemical Society, 117(9), 2479-2490 (1995)
Pentafluorophenyl diphenylphosphinate a new efficient coupling reagent in peptide chemistry.
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Tetrahedron Letters, 32(46), 6711-6714 (1991)
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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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