Fmoc-Asn-OPfp

Base Information

• Chemical Name: Fmoc-Asn-OPfp
• CAS No.: 86060-99-3
• Molecular Formula: C25H17F5N2O5
• Molecular Weight: 520.412
• DSSTox Substance ID: DTXSID60446662
• Wikidata: Q72477993
• Mol file: 86060-99-3.mol

Synonyms:Fmoc-Asn-OPfp;86060-99-3;(2,3,4,5,6-pentafluorophenyl) (2S)-4-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoate;Fmoc-L-asparagine pentafluorophenyl ester;N Alpha-fmoc-L-asparagine pentafluorophenyl ester;DTXSID60446662;MFCD00065625;AKOS015853405;AKOS015902673;FD21197;Nalpha-Fmoc-L-asparagine pentafluorophenyl ester;(S)-perfluorophenyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-amino-4-oxobutanoate

Chemical Property of Fmoc-Asn-OPfp

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 1.41E-19mmHg at 25°C
• Melting Point: ～160℃
• Refractive Index: 1.577
• Boiling Point: 702.4 °C at 760 mmHg
• PKA: 10.02±0.46(Predicted)
• Flash Point: 378.6 °C
• PSA: 107.72000
• Density: 1.478 g/cm³
• LogP: 5.16140
• Storage Temp.: 2-8°C
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 9
• Exact Mass: 520.10576246
• Heavy Atom Count: 37
• Complexity: 814

Purity/Quality:

99%+, ^*data from raw suppliers

Fmoc-Asn-OPfp ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC(=O)N)C(=O)OC4=C(C(=C(C(=C4F)F)F)F)F
• Isomeric SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@@H](CC(=O)N)C(=O)OC4=C(C(=C(C(=C4F)F)F)F)F
• Uses: Fmoc-Asn-Opfp (cas# 86060-99-3) is an L-asparagine derivative and has been used to assess cross-reactivity of cellulose membrane-bound peptides.

Technology Process of Fmoc-Asn-OPfp

There total 1 articles about Fmoc-Asn-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: 96.0%

2,3,4,5,6-pentafluorophenol (771-61-9) + Fmoc-Asn-OH (71989-16-7) → N-α-Fmoc-L-asparagine pentafluorophenyl ester (86060-99-3,200193-34-6)

Guidance literature:

With dicyclohexyl-carbodiimide; In 1,4-dioxane; N,N-dimethyl-formamide; 0 deg C, 1 h; r.t., 1 h;

DOI:10.1055/s-1983-30327

Reference yield:

Fmoc-Tyr(tBu)-OPfp (86060-93-7) + FmocCys(Acm)OPfp (86060-96-0) + N-α-Fmoc-L-asparagine pentafluorophenyl ester (86060-99-3,200193-34-6) + N-α-Fmoc-L-glutamine pentafluorophenyl ester (86061-00-9) → Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Arg-Gly-NH2 (113-79-1,5591-81-1,66513-06-2,66513-07-3,76023-59-1,89576-32-9)

Guidance literature:

Yield given. Multistep reaction; solid phase synthesis;

Reference yield:

Fmoc-Thr(ψ(Me,Me)pro) + Fmoc-Pro-OH (71989-31-6) + N-Fmoc L-Phe (35661-40-6) + Fmoc-Ile-OH (71989-23-6,251316-98-0) + N-α-Fmoc-L-asparagine pentafluorophenyl ester (86060-99-3,200193-34-6) → NH2-Asn-Pro-Phe-Thr(ψ(Me,Me)pro)-Ile-Phe-Pro-OH (1211457-62-3)

Guidance literature:

Fmoc-Pro-OH; With N-ethyl-N,N-diisopropylamine; In dichloromethane; Inert atmosphere; solid phase reaction;

With piperidine; In N,N-dimethyl-formamide; for 0.166667h; Automated synthesizer; solid phase reaction;

Fmoc-Thr(ψ(Me,Me)pro); N-Fmoc L-Phe; Fmoc-Ile-OH; N-α-Fmoc-L-asparagine pentafluorophenyl ester; Further stages;

DOI:10.1016/j.tet.2009.11.090

upstream raw materials:

2,3,4,5,6-pentafluorophenol

Fmoc-Asn-OH

Downstream raw materials:

Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Arg-Gly-NH₂

NH2-Asn-Pro-Phe-Thr(ψ(Me,Me)pro)-Ile-Phe-Pro-OH

NH₂-Asn-Pro-Phe-Thr(tBu)-Ile-Phe-Pro-OH

Refernces