Passa al contenuto
Merck
Tutte le immagini(1)

Documenti fondamentali

418080

Sigma-Aldrich

Pentafluorophenyl diphenylphosphinate

Sinonimo/i:

FDPP, Diphenylphosphinic acid pentafluorophenyl ester

Autenticatiper visualizzare i prezzi riservati alla tua organizzazione & contrattuali


About This Item

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

Stato

solid

Livello qualitativo

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

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)


Scegli una delle versioni più recenti:

Certificati d'analisi (COA)

Lot/Batch Number

Non trovi la versione di tuo interesse?

Se hai bisogno di una versione specifica, puoi cercare il certificato tramite il numero di lotto.

Possiedi già questo prodotto?

I documenti relativi ai prodotti acquistati recentemente sono disponibili nell’Archivio dei documenti.

Visita l’Archivio dei documenti

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

Il team dei nostri ricercatori vanta grande esperienza in tutte le aree della ricerca quali Life Science, scienza dei materiali, sintesi chimica, cromatografia, discipline analitiche, ecc..

Contatta l'Assistenza Tecnica.