Fmoc-Pro-OPfp

Base Information

• Chemical Name: Fmoc-Pro-OPfp
• CAS No.: 86060-90-4
• Molecular Formula: C₂₆H₁₈F₅NO₄
• Molecular Weight: 503.425
• Hs Code.: 29339900
• European Community (EC) Number: 685-323-0
• DSSTox Substance ID: DTXSID30369899
• Nikkaji Number: J3.003.139C
• Wikidata: Q72478736
• Mol file: 86060-90-4.mol

Synonyms:Fmoc-Pro-OPfp;86060-90-4;Fmoc-L-Pro-OPfp;Fmoc-L-proline pentafluorophenyl ester;1-O-(9H-fluoren-9-ylmethyl) 2-O-(2,3,4,5,6-pentafluorophenyl) (2S)-pyrrolidine-1,2-dicarboxylate;N-alpha-(9-Fluorenylmethyloxycarbonyl)-L-proline pentafluorphenyl ester;SCHEMBL3056823;Fmoc-Pro-OPfp, >=96.0%;DTXSID30369899;CQBLOHXKGUNWRV-SFHVURJKSA-N;N-(9-Fluorenylmethoxycarbonyl)-L-proline pentafluorophenyl ester;MFCD00065672;AKOS015902492;CS-W013823;HY-W013107;DS-16204;F11064;1-(9H-Fluorene-9-ylmethoxycarbonyl)-L-proline pentafluorophenyl ester;(S)-1-(9H-fluoren-9-yl)methyl 2-perfluorophenyl pyrrolidine-1,2-dicarboxylate;1,2-Pyrrolidinedicarboxylicacid,1-(9H-fluoren-9-ylmethyl)2-(pentafluorophenyl)ester,(2S)-

Chemical Property of Fmoc-Pro-OPfp

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 3.77E-13mmHg at 25°C
• Melting Point: 127-129 °C
• Refractive Index: 1.582
• Boiling Point: 573.3 °C at 760 mmHg
• Flash Point: 300.5 °C
• PSA: 55.84000
• Density: 1.455 g/cm³
• LogP: 5.63890
• Storage Temp.: 2-8°C
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 503.11559887
• Heavy Atom Count: 36
• Complexity: 781

Purity/Quality:

99%+, ^*data from raw suppliers

Fmoc-Pro-OPfp Novabiochem? ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(N(C1)C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)C(=O)OC5=C(C(=C(C(=C5F)F)F)F)F
• Isomeric SMILES: C1C[C@H](N(C1)C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)C(=O)OC5=C(C(=C(C(=C5F)F)F)F)F

Technology Process of Fmoc-Pro-OPfp

There total 5 articles about Fmoc-Pro-OPfp which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2,3,4,5,6-pentafluorophenol (771-61-9) + Fmoc-Pro-OH (71989-31-6) → Fmoc-L-proline pentafluorophenyl ester (125281-38-1,86060-90-4)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; for 1h;

DOI:10.1016/S0040-4020(99)00650-X

Reference yield: 84.0%

2,3,4,5,6-pentafluorophenol (771-61-9) + (S)-N-(fluoren-9-ylmethoxycarbonyl)prolyl chloride (103321-52-4) → Fmoc-L-proline pentafluorophenyl ester (125281-38-1,86060-90-4)

Guidance literature:

With pyridine; In tetrahydrofuran; at 4 ℃;

DOI:10.1016/0040-4039(91)80788-8

Reference yield:

Fmoc-Pro-OH (71989-31-6) → Fmoc-L-proline pentafluorophenyl ester (125281-38-1,86060-90-4)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂, pyridine / CH₂Cl₂ / Heating

2: 84 percent / pyridine / tetrahydrofuran / 4 °C

With pyridine; thionyl chloride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0040-4039(91)80788-8

upstream raw materials:

2,3,4,5,6-pentafluorophenol

Fmoc-Pro-OH

(S)-N-(fluoren-9-ylmethoxycarbonyl)prolyl chloride

(9-fluorenyl)methyl pentafluorophenyl carbonate

Downstream raw materials:

Pro-Thr-Tyr-Pro-Thr-α-N-(octyloxybenzoyl)-Orn

N-(9-fluorenylmethoxycarbonyl)-L-prolyl-N-ethyl-S-triphenyl-methyl-L-cysteine

C₆₉H₁₀₄N₁₈O₁₅S

C₈₂H₁₁₅N₂₁O₁₆S

Refernces

• 1、 Jacobsen, Mogens Havsteen,Buchardt, Ole,Engdahl, Tom,Holm, Arne. "A new facile one-pot preparation of pentafluorophenyl (Pfp) and 3,4-dihydro-4-oxo-1,2,3-benzotriazine-3-yl (Dhbt) esters of Fmoc amino acids". . p. 6199 - 6202. Retrieved 2007/10/02.
• 2、 Kisfaludy, Lajos,Schoen, Istvan. "Preparation and Applications of Pentafluorophenyl Esters of 9-Fluorenylmethyloxycarbonyl Amino Acids for Peptide Synthesis". . p. 325 - 327. Retrieved 2007/10/02.