Fmoc-Cys(Bzl)-OPfp

Base Information

• Chemical Name: Fmoc-Cys(Bzl)-OPfp
• CAS No.: 86060-95-9
• Molecular Formula: C31H22 F5 N O4 S
• Molecular Weight: 599.57
• DSSTox Substance ID: DTXSID90583796
• Wikidata: Q82475396
• Mol file: 86060-95-9.mol

Synonyms:Fmoc-Cys(Bzl)-OPfp;86060-95-9;(2,3,4,5,6-pentafluorophenyl) (2R)-3-benzylsulfanyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate;Fmoc-S-benzyl-L-cysteine pentafluorophenyl ester;DTXSID90583796;HY-W141783;CS-0201581;Fmoc-S-benzyl-L-cysteine pentafluorophenyl esterl;Fmoc-Cys(Bzl)-OPfp, purum, >=98.0% (HPLC);(R)-perfluorophenyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(benzylthio)propanoate;Pentafluorophenyl S-benzyl-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-cysteinate;pentafluorophenyl (2R)-3-(benzylsulfanyl)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propanoate

Chemical Property of Fmoc-Cys(Bzl)-OPfp

Chemical Property:

• Boiling Point: 703.7±60.0 °C(Predicted)
• PKA: 9.94±0.46(Predicted)
• PSA: 89.93000
• Density: 1.407±0.06 g/cm3(Predicted)
• LogP: 7.51910
• Storage Temp.: 2-8°C
• XLogP3: 7.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 11
• Exact Mass: 599.11897017
• Heavy Atom Count: 42
• Complexity: 875

Purity/Quality:

99% ^*data from raw suppliers

(R)-Perfluorophenyl2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(benzylthio)propanoate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CSCC(C(=O)OC2=C(C(=C(C(=C2F)F)F)F)F)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35
• Isomeric SMILES: C1=CC=C(C=C1)CSC[C@@H](C(=O)OC2=C(C(=C(C(=C2F)F)F)F)F)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35

Technology Process of Fmoc-Cys(Bzl)-OPfp

There total 3 articles about Fmoc-Cys(Bzl)-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: 89.0%

2,3,4,5,6-pentafluorophenol (771-61-9) + Nα-Fmoc-S-benzylcysteine (53298-33-2,252049-18-6) → Fmoc-Cys(Bzl)-OPfp (86060-95-9)

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-benzyl-L-cysteine (3054-01-1,25988-62-9) → Fmoc-Cys(Bzl)-OPfp (86060-95-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent

2: 89 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:

(9-fluorenyl)methyl pentafluorophenyl carbonate (88744-04-1) → Fmoc-Cys(Bzl)-OPfp (86060-95-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / NaHCO₃ / H₂O; acetone / Ambient temperature

2: dicyclohexylcarbodiimide / ethyl acetate / 2 h / 0 °C

With sodium hydrogencarbonate; dicyclohexyl-carbodiimide; In water; ethyl acetate; acetone;

upstream raw materials:

2,3,4,5,6-pentafluorophenol

N^α-Fmoc-S-benzylcysteine

S-benzyl-L-cysteine

(9-fluorenyl)methyl pentafluorophenyl carbonate

Downstream raw materials:

Fmoc-Cys(Bzl)-Met-Thr(Bzl)-Thr(Bzl)-Ala-Gln-Gly-O^tBu

Fmoc-Cys(Bzl)-Met-Thr-Thr-Ala-Gln-Gly-O^tBu

Refernces

• 1、 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.