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418080

Sigma-Aldrich

Pentafluorophenyl diphenylphosphinate

Sinonimo/i:

FDPP, Diphenylphosphinic acid pentafluorophenyl ester

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About This Item

Formula condensata:
(C6H5)2P(O)OC6F5
Numero CAS:
138687-69-1
Peso molecolare:
384.24
Numero MDL:
MFCD00192380
Codice UNSPSC:
12352101
ID PubChem:
24866201
NACRES:
NA.22

Stato

solid

Livello qualitativo

100

Punto di fusione

47-50 °C (lit.)

Gruppo funzionale

fluoro

Stringa SMILE

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
OOWSDKUFKGVADH-UHFFFAOYSA-N

Categorie correlate

Descrizione generale

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.

Applicazioni

Catalyst involved in coupling and macrocyclization

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.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

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Certificati d'analisi (COA)

Lot/Batch Number
MKCD1296
MKCC3889
MKBW7753V
MKBW9437V
MKBL2283V

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Highly convergent route to cyclopeptide alkaloids. Total synthesis of ziziphine N.
He G, et al.
Organic Letters, 9(7), 1367-1369 (2007)
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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