Fmoc-Ile-OPfp

Base Information

• Chemical Name: Fmoc-Ile-OPfp
• CAS No.: 86060-89-1
• Molecular Formula: C27H22F5NO4
• Molecular Weight: 519.468
• Hs Code.: 2924 29 70
• European Community (EC) Number: 685-326-7
• DSSTox Substance ID: DTXSID60544410
• Mol file: 86060-89-1.mol

Synonyms:Fmoc-Ile-OPfp;86060-89-1;Fmoc-L-isoleucine pentafluorophenyl ester;(2,3,4,5,6-pentafluorophenyl) (2S,3S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylpentanoate;Fmoc-lle-OPfp;FMOC-ILE-OPFP ACETATE SALT;Fmoc-L-Ile-OPfp;SCHEMBL3060107;DTXSID60544410;AMY22723;MFCD00077063;AKOS015853372;AKOS015902491;FD21833;Fmoc-Ile-OPfp, >=98.0% (TLC);M06248;A863328;Pentafluorophenyl N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-isoleucinate;(2S,3S)-perfluorophenyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-methylpentanoate;L-Isoleucine,N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, pentafluorophenyl ester (9CI);N-alpha-(9-Fluorenylmethyloxycarbonyl)-L-isoleucine pentafluorphenyl ester (Fmoc-L-Ile-OPfp)

Chemical Property of Fmoc-Ile-OPfp

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 3.47E-14mmHg at 25°C
• Melting Point: 73-75℃
• Refractive Index: 1.549
• Boiling Point: 596.3 °C at 760 mmHg
• Flash Point: 314.5 °C
• PSA: 64.63000
• Density: 1.35 g/cm³
• LogP: 6.63180
• Storage Temp.: 2-8°C
• XLogP3: 6.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 519.14689899
• Heavy Atom Count: 37
• Complexity: 767

Purity/Quality:

99%+, ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C(C(=O)OC1=C(C(=C(C(=C1F)F)F)F)F)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Isomeric SMILES: CC[C@H](C)[C@@H](C(=O)OC1=C(C(=C(C(=C1F)F)F)F)F)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Technology Process of Fmoc-Ile-OPfp

There total 5 articles about Fmoc-Ile-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: 99.0%

pentafluorophenyl trifloroacetate (14533-84-7) + Fmoc-Ile-OH (71989-23-6,251316-98-0) → N-α-Fmoc-L-isoleucine pentafluorophenyl ester (86060-89-1)

Guidance literature:

With pyridine; In N,N-dimethyl-formamide; for 0.75h; Ambient temperature;

DOI:10.1016/S0040-4039(00)97976-0

Reference yield: 78.0%

2,3,4,5,6-pentafluorophenol (771-61-9) + Fmoc-Ile-OH (71989-23-6,251316-98-0) → N-α-Fmoc-L-isoleucine pentafluorophenyl ester (86060-89-1)

Guidance literature:

With dicyclohexyl-carbodiimide; In ethyl acetate; 0 deg C, 1 h; r.t., 1 h;

DOI:10.1055/s-1983-30327

Reference yield:

Fmoc-Ile-OH (71989-23-6,251316-98-0) → N-α-Fmoc-L-isoleucine pentafluorophenyl ester (86060-89-1)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂, pyridine / CH₂Cl₂ / Heating

2: 81 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-Ile-OH

pentafluorophenyl trifloroacetate

L-isoleucine

Downstream raw materials:

H_.Val_.Gln_.Ala_.Ala_.Ile_.Asp_.Tyr_.Ile_.Asn_.Gly_.OH

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

H-Phe-Val-Trp-Ile-NH₂

Refernces

• 1、 Green, Michael,Berman, Judd. "PREPARATION OF PENTAFLUOROPHENYL ESTERS OF FMOC PROTECTED AMINO ACIDS WITH PENTAFLUOROPHENYL TRIFLUOROACETATE". . p. 5851 - 5852. 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.