Fmoc-3-fluoro-L-phenylalanine

Base Information

• Chemical Name: Fmoc-3-fluoro-L-phenylalanine
• CAS No.: 198560-68-8
• Molecular Formula: C₂₄H₂₀FNO₄
• Molecular Weight: 405.426
• Hs Code.: 2924299090
• European Community (EC) Number: 692-465-7
• DSSTox Substance ID: DTXSID90370320
• Nikkaji Number: J2.944.399H
• Wikidata: Q72478341
• Mol file: 198560-68-8.mol

Synonyms:198560-68-8;Fmoc-3-fluoro-L-phenylalanine;Fmoc-Phe(3-F)-OH;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(3-fluorophenyl)propanoic acid;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(3-fluorophenyl)propanoic acid;FMOC-3-FLUORO-L-PHE;Fmoc-L-3-Fluorophenylalanine;L-Phenylalanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-3-fluoro-;FMOC-M-FLUORO-PHE-OH;Fmoc-L-phe(3-F)-OH;Fmoc-3-Fluoro-L-Phe-OH;L-Fmoc-3-fluorophenylalanine;SCHEMBL118332;DTXSID90370320;MFCD00672328;AKOS015837256;AKOS015908848;AC-5832;AM83340;CS-W009714;DS-16171;A50193;Fmoc-Phe(3-F)-OH, >=97.0% (HPLC);EN300-3428340;J-300402;(2S)-2-({[(9H-Fluoren-9-yl)methoxy]carbonyl}amino)-3-(3-fluorophenyl)propanoic acid;(S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-3-(3-FLUOROPHENYL)PROPANOIC ACID;N-alpha-(9-Fluorenylmethyloxycarbonyl)-L-3-fluoro-phenylalanine (Fmoc-L-Phe(3-F)-OH)

Chemical Property of Fmoc-3-fluoro-L-phenylalanine

Chemical Property:

• Vapor Pressure: 3.89E-16mmHg at 25°C
• Melting Point: 155.8 °C
• Boiling Point: 618.1 °C at 760 mmHg
• PKA: 3.70±0.10(Predicted)
• Flash Point: 327.6 °C
• PSA: 75.63000
• Density: 1.317 g/cm³
• LogP: 4.75100
• Storage Temp.: 2-8°C
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 405.13763628
• Heavy Atom Count: 30
• Complexity: 592

Purity/Quality:

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

Fmoc-3-fluoro-l-phenylalanine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CC(=CC=C4)F)C(=O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@@H](CC4=CC(=CC=C4)F)C(=O)O

Technology Process of Fmoc-3-fluoro-L-phenylalanine

There total 9 articles about Fmoc-3-fluoro-L-phenylalanine 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:

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + L-3-fluorophenylalanine (19883-77-3,2629-54-1) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(3-fluorophenyl)propanoic acid (198560-68-8)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 0 - 25 ℃; for 22h;

DOI:10.1016/j.bmc.2018.03.023

Reference yield:

3-fluorophenylalanine (456-88-2,2629-54-1) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → Fmoc-Phe(3-F)-OH (198560-68-8)

Guidance literature:

With phosphate buffer; In N,N-dimethyl-formamide; at 0 ℃; for 24h; pH=9 - 10;

DOI:10.1021/ja0348391

Reference yield:

Fmoc-3-F-Phe-OMe (1284236-47-0) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(3-fluorophenyl)propanoic acid (198560-68-8)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 0 ℃; for 1h;

DOI:10.1021/ja512690x

upstream raw materials:

3-fluorophenylalanine

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

1-Fluoro-3-iodobenzene

Fmoc-3-F-Phe-OMe

Refernces

• 1、 Meng, Kaicheng,Shim, Paul,Wang, Qingtin,Zhao, Shuai,Gu, Ting,Kahsai, Alem W.,Ahn, Seungkirl,Chen, Xin. "Design, synthesis, and functional assessment of Cmpd-15 derivatives as negative allosteric modulators for the β2-adrenergic receptor". . p. 2320 - 2330. Retrieved 2018/03/29.
• 2、 -. "LIGAND-CONTROLLED C(SP3)-H ARYLATION AND OLEFINATION IN SYNTHESIS OF UNNATURAL CHIRAL ALPHA AMINO ACIDS". Page/Page column 236; 238; 239; 240. . Retrieved 2015/10/05.