Fmoc-Cys(Acm)-OPfp

Base Information

• Chemical Name: Fmoc-Cys(Acm)-OPfp
• CAS No.: 86060-96-0
• Molecular Formula: C27H21F5N2O5S
• Molecular Weight: 580.532
• Hs Code.: 29349990
• DSSTox Substance ID: DTXSID60553926
• Nikkaji Number: J1.043.272C
• Wikidata: Q72477691
• Mol file: 86060-96-0.mol

Synonyms:Fmoc-Cys(Acm)-OPfp;86060-96-0;(2,3,4,5,6-pentafluorophenyl) (2R)-3-(acetamidomethylsulfanyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate;Fmoc-S-acetamidomethyl-L-cysteine pentafluorophenyl ester;DTXSID60553926;(R)-perfluorophenyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(acetamidomethylthio)propanoate;AKOS015853225;AKOS015902630;CS-0456356;Pentafluorophenyl S-(acetamidomethyl)-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-cysteinate;Perfluorophenyl N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-(acetamidomethyl)-L-cysteinate

Chemical Property of Fmoc-Cys(Acm)-OPfp

Chemical Property:

• Vapor Pressure: 6.54E-22mmHg at 25°C
• Refractive Index: 1.578
• Boiling Point: 742.4 °C at 760 mmHg
• Flash Point: 402.8 °C
• PSA: 119.03000
• Density: 1.436 g/cm³
• LogP: 5.80340
• Storage Temp.: 2-8°C
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 11
• Exact Mass: 580.10913376
• Heavy Atom Count: 40
• Complexity: 867

Purity/Quality:

99%+, ^*data from raw suppliers

Fmoc-Cys(Acm)-Opfp ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NCSCC(C(=O)OC1=C(C(=C(C(=C1F)F)F)F)F)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Isomeric SMILES: CC(=O)NCSC[C@@H](C(=O)OC1=C(C(=C(C(=C1F)F)F)F)F)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Uses: Fmoc-Cys(Acm)-Opfp (cas# 86060-96-0) is a cysteine derivative and a useful building block used in the synthesis of self-assembling pH-sensitive micelles.

Technology Process of Fmoc-Cys(Acm)-OPfp

There total 2 articles about Fmoc-Cys(Acm)-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: 78.0%

2,3,4,5,6-pentafluorophenol (771-61-9) + S-[(acetylamino)methyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-cysteine (86060-81-3) → FmocCys(Acm)OPfp (86060-96-0)

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:

S-acetamidomethyl-L-cysteine (19647-70-2) → FmocCys(Acm)OPfp (86060-96-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent

2: 78 percent / dicyclohexylcarbodiimide / ethyl acetate / 0 deg C, 1 h; r.t., 1 h

With dicyclohexyl-carbodiimide; In ethyl acetate;

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;

upstream raw materials:

2,3,4,5,6-pentafluorophenol

S-[(acetylamino)methyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-cysteine

S-acetamidomethyl-L-cysteine

Downstream raw materials:

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

Refernces