Fmoc-L-3-Cyanophenylalanine

Base Information

• Chemical Name: Fmoc-L-3-Cyanophenylalanine
• CAS No.: 205526-36-9
• Molecular Formula: C25H20N2O4
• Molecular Weight: 412.445
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID50426256
• Wikidata: Q72478221
• Mol file: 205526-36-9.mol

Synonyms:205526-36-9;Fmoc-L-3-Cyanophenylalanine;Fmoc-3-cyano-L-phenylalanine;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(3-cyanophenyl)propanoic acid;Fmoc-Phe(3-CN)-OH;(2S)-3-(3-cyanophenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid;Fmoc-L-3-cyanophenylalanin;SCHEMBL120479;DTXSID50426256;CVLOUTPKZUJTGV-QHCPKHFHSA-N;L-Phenylalanine, 3-cyano-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-;MFCD00797585;AKOS015837240;AKOS015912006;AC-9891;AM82769;CS-W011674;HY-W010958;DS-18385;A50192;EN300-7374635;A814688;J-013412;J-013413;3-cyano-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-phenylalanine;(2S)-3-(3-cyanophenyl)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanoic acid;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(3-cyanophenyl)propanoicacid

Chemical Property of Fmoc-L-3-Cyanophenylalanine

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 6.61E-19mmHg at 25°C
• Melting Point: 115.6 °C
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 670.7 °C at 760 mmHg
• PKA: 3?+-.0.10(Predicted)
• Flash Point: 359.5 °C
• PSA: 99.42000
• Density: 1.35 g/cm³
• LogP: 4.48358
• Storage Temp.: 2-8°C
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 412.14230712
• Heavy Atom Count: 31
• Complexity: 679

Purity/Quality:

98%,99%, ^*data from raw suppliers

Fmoc-L-3-cyanophenylalanine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CC(=CC=C4)C#N)C(=O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@@H](CC4=CC(=CC=C4)C#N)C(=O)O
• Uses: Fmoc-L-3-cyanophenylalanine is an intermediate used in the preparation of phenylalanine and phenylglycine derivatives as arginine mimetics in tripeptides as dengue protease inhibitors.

Technology Process of Fmoc-L-3-Cyanophenylalanine

There total 1 articles about Fmoc-L-3-Cyanophenylalanine 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%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + 3-cyano-(D,L)-phenylalanine (57213-48-6) → Fmoc-(3-cyano)-L-phenylalanine (205526-36-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In water; acetonitrile; at 20 ℃; for 1h;

DOI:10.1021/acs.jmedchem.5b00612

Reference yield: 100.0%

2-chlorotrityl chloride polystyrene resin + Fmoc-(3-cyano)-L-phenylalanine (205526-36-9) → C25H19N2O3Pol

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 18 - 25 ℃; 2-chlorotrityl chloride resin

Reference yield: 91.0%

Fmoc-(3-cyano)-L-phenylalanine (205526-36-9) → (S)-2-(((9H-fluoren-9-yl)methoxy)carbonyl)-3-(3-(N'-hydroxycarbamimidoyl)phenyl)propanoic acid

Guidance literature:

With hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine; In ethanol; at 20 - 60 ℃;

DOI:10.1016/j.tetlet.2021.153342

upstream raw materials:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

3-cyano-(D,L)-phenylalanine

Downstream raw materials:

DT₁₀₅₈-125-3

Refernces

• 1、 Weigel, Lena F.,Nitsche, Christoph,Graf, Dominik,Bartenschlager, Ralf,Klein, Christian D.. "Phenylalanine and Phenylglycine Analogues as Arginine Mimetics in Dengue Protease Inhibitors". supporting information. p. 7719 - 7733. Retrieved 2015/10/20.