418080
Pentafluorophenyl diphenylphosphinate
Synonym(s):
FDPP, Diphenylphosphinic acid pentafluorophenyl ester
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About This Item
Linear Formula:
(C6H5)2P(O)OC6F5
CAS Number:
Molecular Weight:
384.24
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352101
MDL number:
Form:
solid
form
solid
Quality Level
mp
47-50 °C (lit.)
functional group
fluoro
SMILES string
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
InChI key
OOWSDKUFKGVADH-UHFFFAOYSA-N
General description
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.
Application
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.
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
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Pentafluorophenyl Diphenylphosphinate (FDPP)
Leonard MS, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition, 1-8 (2001)
Pentafluorophenyl Diphenylphosphinate (FDPP).
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2002)
A new synthesis of cyclotheonamide B via guanidination of ornithine
Jingen, Deng and Yasumasa, Hamada and Takayuki, Shioiri
Tetrahedron Letters, 37(13), 2261-2264 (1996)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 418080-5G | 04061833372524 |
| 418080-1G | 04061826672013 |