Fmoc-L-beta-homophenylalanine

Base Information

• Chemical Name: Fmoc-L-beta-homophenylalanine
• CAS No.: 193954-28-8
• Molecular Formula: C25H23NO4
• Molecular Weight: 401.462
• European Community (EC) Number: 888-855-3
• DSSTox Substance ID: DTXSID00375821
• Nikkaji Number: J868.553C
• Wikidata: Q72478471
• Mol file: 193954-28-8.mol

Synonyms:Fmoc-L-beta-homophenylalanine;193954-28-8;Fmoc-B-HoPhe-OH;(3S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-phenylbutanoic acid;(S)-3-(Fmoc-amino)-4-phenylbutanoic acid;MFCD01863055;(S)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-phenylbutanoic acid;(S)-3-[[[(9H-Fluoren-9-yl)methoxy]carbonyl]amino]-4-phenylbutanoic acid;Fmoc-L-beta-HomoPhe-OH;Fmoc-Phe-(C#CH2)OH;Fmoc-L- beta -HPhe-OH;SCHEMBL119394;N-Fmoc-L-beta-homophenylalanine;DTXSID00375821;(3S)-3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-4-phenylbutanoic acid;AKOS016843069;CS-W009722;HY-W009006;(S)-Fmoc-3-amino-4-phenylbutyric acid;AC-22087;DS-18586;Fmoc-beta-Homophe-OH, >=95.0% (HPLC);EN300-637470;A813686;(s)-3-(9h-fluoren-9-ylmethoxycarbonylamino)-4-phenyl-butyric acid;(S)-3-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-phenylbutyric acid;(S)-beta-(9H-Fluorene-9-ylmethoxycarbonylamino)benzenebutyric acid;(3S)-3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-phenylbutanoic acid

Chemical Property of Fmoc-L-beta-homophenylalanine

Chemical Property:

• Vapor Pressure: 6.64E-17mmHg at 25°C
• Melting Point: 110-112 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• Refractive Index: 1.624
• Boiling Point: 633.217 °C at 760 mmHg
• PKA: 4.38±0.10(Predicted)
• Flash Point: 336.758 °C
• PSA: 75.63000
• Density: 1.255 g/cm³
• LogP: 5.00200
• Storage Temp.: 2-8°C
• Water Solubility.: Slightly soluble in water.
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 401.16270821
• Heavy Atom Count: 30
• Complexity: 566

Purity/Quality:

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

Fmoc-L-beta-homophenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(CC(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H](CC(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Uses: N-Fmoc-L-beta-homophenylalanine is used for producing high quality peptides.

Technology Process of Fmoc-L-beta-homophenylalanine

There total 10 articles about Fmoc-L-beta-homophenylalanine 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: 97.0%

(S)-1-diazo-3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-phenylbutan-2-one (172097-41-5) → (S)-3-(9H-fluoren-9-yl)methoxycarbonylamino-4-phenylbutanoic acid (193954-28-8,282524-78-1)

Guidance literature:

With water; silver trifluoromethanesulfonate; In 1,4-dioxane; for 72h; sonication;

DOI:10.1021/ja029205t

Reference yield: 58.0%

allyl (S)-3-(9H-fluoren-9-yl)methoxycarbonylamino-4-phenylbutanoate → (S)-3-(9H-fluoren-9-yl)methoxycarbonylamino-4-phenylbutanoic acid (193954-28-8,282524-78-1)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tri-n-butyl-tin hydride; In dichloromethane; for 0.166667h;

DOI:10.1016/S0040-4020(01)00731-1

Reference yield:

N-Fmoc L-Phe (35661-40-6) → (S)-3-(9H-fluoren-9-yl)methoxycarbonylamino-4-phenylbutanoic acid (193954-28-8,282524-78-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / 1H-benzotriazol-1-yl-N-oxytrispyrrolidinophosphonium PF₆^(1-); N-ethyldiisopropylamine / tetrahydrofuran; dimethylformamide; diethyl ether / 0.25 h / 0 °C

2: 85 percent / silver benzoate / dioxane; H₂O / 70 °C

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; silver benzoate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; diethyl ether; water; N,N-dimethyl-formamide; 2: Wolff rearrangement;

upstream raw materials:

(S)-1-diazo-3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-phenylbutan-2-one

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

(S)-3-amino-4-phenylbutanoic acid trifluoroacetate

N-Fmoc L-Phe

Refernces

• 1、 Kantharaju,Suresh Babu, Vommina V.. "Homologation of α-amino acids to β-amino acids: 9-Fluorenylmethyl chloroformate as a carboxyl group activating agent for the synthesis of Nα-protected aminoacyldiazomethanes". . p. 2152 - 2158. Retrieved 2007/10/03.
• 2、 Arvidsson, Per I.,Frackenpohl, Jens,Seebach, Dieter. "Syntheses and CD-spectroscopic investigations of longer-chain β-peptides: Preparation by solid-phase couplings of single amino acids, dipeptides, and tripeptides". . p. 1522 - 1553. Retrieved 2007/10/03.