418080

Pentafluorophenyl diphenylphosphinate

• 동의어(들): FDPP, Diphenylphosphinic acid pentafluorophenyl ester
• Linear Formula: (C₆H₅)₂P(O)OC₆F₅
• CAS Number: 138687-69-1
• Molecular Weight: 384.24
• MDL number: MFCD00192380
• UNSPSC 코드: 12352101
• PubChem Substance ID: 24866201
• NACRES: NA.22

속성

• 형태: solid
• Quality Level: 100
• mp: 47-50 °C (lit.)
• 작용기: 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

설명

일반 설명

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.

애플리케이션

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.

안전성 정보

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable
• 개인 보호 장비: Eyeshields, Gloves, type N95 (US)