138687-69-1 Usage
Description
Pentafluorophenyl diphenylphosphinate (FDPP) is a reagent used as a carboxyl activating group and a coupling agent in a variety of amide bond formations. It is a white to yellow solid and can be prepared from diphenylphosphinic chloride and pentafluorophenol in the presence of imidazole. FDPP is known for its ability to form amide bonds without racemization, making it a valuable tool in the synthesis of various compounds.
Uses
Used in Pharmaceutical Industry:
PENTAFLUOROPHENYL DIPHENYLPHOSPHINATE is used as a coupling agent for the synthesis of peptides by solid-phase and solution-phase reactions. It is particularly useful in the preparation of macrocyclic peptide cyclotheonamide B, which serves as a thrombin inhibitor. This application takes advantage of FDPP's ability to form amide bonds without racemization, ensuring the optical purity of the final product.
Used in Chemical Synthesis:
PENTAFLUOROPHENYL DIPHENYLPHOSPHINATE is used as a coupling reagent in the cyclooligomerization of N-methylated-L-valine thiazole amino acid to obtain its cyclic tetramers. This process is crucial for the development of complex molecular structures with potential applications in various fields.
Used in Total Synthesis:
PENTAFLUOROPHENYL DIPHENYLPHOSPHINATE is used as a coupling agent in the macrocyclization of an intermediate for the total synthesis of ziziphine N. This application highlights FDPP's role in the formation of complex cyclic compounds, which are often found in natural products with biological activity.
Used in Macrolactamization:
PENTAFLUOROPHENYL DIPHENYLPHOSPHINATE is used as a coupling agent for the macrolactamization of a precursor in synthesizing cryptophycin D. This process is essential for the production of macrolactams, which are important components in various pharmaceutical compounds.
Check Digit Verification of cas no
The CAS Registry Mumber 138687-69-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,8,6,8 and 7 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 138687-69:
(8*1)+(7*3)+(6*8)+(5*6)+(4*8)+(3*7)+(2*6)+(1*9)=181
181 % 10 = 1
So 138687-69-1 is a valid CAS Registry Number.
InChI:InChI=1/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
138687-69-1Relevant articles and documents
Total synthesis of cryptophycins. Revision of the structures of cryptophycins A and C
Barrow, Russell A.,Hemscheidt, Thomas,Liang, Jian,Paik, Seunguk,Moore, Richard E.,Tius, Marcus A.
, p. 2479 - 2490 (2007/10/02)
The convergent total synthesis of cryptophycins C and D is described. It has been shown that in both natural products the absolute configuration of the α-amino acid corresponds to the D-series. The structural assignment for cryptophycin C has been correct
PENTAFLUOROPHENYL DIPHENYLPHOSPHINATE A NEW EFFICIENT COUPLING REAGENT IN PEPTIDE CHEMISTRY
Chen, Shaoqing,Xu, Jiecheng
, p. 6711 - 6714 (2007/10/02)
Pentafluorophenyl diphenylphosphinate was found to be a new efficient coupling reagent for the racemization-free synthesis of peptides.It has been applied in both the solution and the solid phase peptide synthesis.
