(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-([1,1'-biphenyl]-4-yl)propanoic acid

Base Information

• Chemical Name: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-([1,1'-biphenyl]-4-yl)propanoic acid
• CAS No.: 199110-64-0
• Molecular Formula: C30H25NO4
• Molecular Weight: 463.533
• Hs Code.: 2922498590
• European Community (EC) Number: 845-990-2
• Nikkaji Number: J1.112.469K
• Mol file: 199110-64-0.mol

Synonyms:199110-64-0;Fmoc-Bip(4,4')-OH;Fmoc-L-4,4'-Biphenylalanine;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-([1,1'-biphenyl]-4-yl)propanoic acid;FMOC-P-PHENYL-L-PHENYLALANINE;FMOC-4-BIPHENYL-L-ALA;3-(4-BIPHENYLYL)-N-FMOC-L-ALANINE;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-phenylphenyl)propanoic acid;Fmoc-4-phenyl-D-Phe-OH;FMOC-BIP-OH;MFCD00191198;FMOC-BPH-OH;SCHEMBL800116;VSGACONKQRJFGX-NDEPHWFRSA-N;BCP11626;AKOS015901031;AC-9871;CS-W011552;HY-W010836;FMOC-L-ALA(4,4'-BIPHENYL)-OH;[1,1'-Biphenyl]-4-propanoic acid, alpha-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-, (alphaS)-;AS-15810;Fmoc--(4-biphenylyl)-D-Ala-OH;Fmoc-D-Bip-OH;A814061;J-012864;N-(9H-Fluoren-9-ylmethoxycarbonyl)-4-phenyl-L-phenylalanine;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-L-BIPHENYLALANINE;FMOC-(S)-2-AMINO-3-(1,1'-BIPHENY-4-YL)PROPANOIC ACID;(S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-3-(BIPHENYL-4-YL)PROPANOIC ACID;3-(4-Biphenylyl)-N-Fmoc-L-Alanine

Chemical Property of (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-([1,1'-biphenyl]-4-yl)propanoic acid

Chemical Property:

• Vapor Pressure: 2.13E-27mmHg at 25°C
• Refractive Index: 1.651
• Boiling Point: 700.7 °C at 760 mmHg
• PKA: 3.77±0.10(Predicted)
• Flash Point: 377.6 °C
• PSA: 75.63000
• Density: 1.257 g/cm³
• LogP: 6.27890
• Storage Temp.: 2-8°C
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 463.17835828
• Heavy Atom Count: 35
• Complexity: 689

Purity/Quality:

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

Fmoc-l-4,4''-biphenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC=C(C=C2)CC(C(=O)O)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35
• Isomeric SMILES: C1=CC=C(C=C1)C2=CC=C(C=C2)C[C@@H](C(=O)O)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35
• Uses: Fmoc-l-4,4''-biphenylalanine

Technology Process of (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-([1,1'-biphenyl]-4-yl)propanoic acid

There total 7 articles about (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-([1,1'-biphenyl]-4-yl)propanoic acid 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%

Fmoc-4-bromo-L-phenylalanine (198561-04-5) + phenylboronic acid (98-80-6) → (S)-3-biphenyl-4-yl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid (199110-64-0,205526-38-1)

Guidance literature:

With potassium phosphate; 1,1'-bis(di-tertbutylphosphino)ferrocene; palladium diacetate; In tetrahydrofuran; at 50 ℃; for 16h; Reagent/catalyst; Solvent; Inert atmosphere;

DOI:10.1021/acs.joc.6b01965

Reference yield: 67.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (S)-3-([1,1'-biphenyl]-3-yl)-2-aminopropanoic acid (164172-95-6,164172-96-7,887502-03-6) → (S)-3-biphenyl-4-yl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid (199110-64-0,205526-38-1)

Guidance literature:

With sodium carbonate; In water; acetone; at 20 ℃;

DOI:10.1021/acs.jmedchem.0c01941

Reference yield:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → (S)-3-biphenyl-4-yl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid (199110-64-0,205526-38-1)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium carbonate / water; acetone / 2 h / 20 °C

2: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; isopropyl alcohol / 5 h / 20 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; potassium carbonate; In water; isopropyl alcohol; acetone;

DOI:10.1002/anie.201812348

upstream raw materials:

Fmoc-4-bromo-L-phenylalanine

phenylboronic acid

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

H-p-BrPhe-OH

Downstream raw materials:

(S)-N-((S)-1-amino-3-(biphenyl-4-yl)-1-oxopropan-2-yl)-5-guanidino-2-((2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)pentanamide

(S)-2-((S)-3-(biphenyl-4-yl)-2-((2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)propanamido)-5-guanidinopentanamide

Refernces

• 1、 Tran, Kien,Van Den Hauwe, Robin,Sainsily, Xavier,Couvineau, Pierre,C?té, Jér?me,Simard, Louise,Echevarria, Marco,Murza, Alexandre,Serre, Alexandra,Théroux, Léa,Saibi, Sabrina,Haroune, Lounès,Longpré, Jean-Michel,Lesur, Olivier,Auger-Messier, Mannix,Spino, Claude,Bouvier, Michel,Sarret, Philippe,Ballet, Steven,Marsault, éric. "Constraining the Side Chain of C-Terminal Amino Acids in Apelin-13 Greatly Increases Affinity, Modulates Signaling, and Improves the Pharmacokinetic Profile". supporting information. p. 5345 - 5364. Retrieved 2021/02/16.
• 2、 -. "Ligands for opioid receptors". . . Retrieved 2008/06/13.