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

Base Information

• Chemical Name: (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-([1,1'-biphenyl]-4-yl)propanoic acid
• CAS No.: 205526-38-1
• Molecular Formula: C₃₀H₂₅NO₄
• Molecular Weight: 463.533
• European Community (EC) Number: 845-990-2
• DSSTox Substance ID: DTXSID501133710
• Mol file: 205526-38-1.mol

Synonyms:205526-38-1;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-([1,1'-biphenyl]-4-yl)propanoic acid;Fmoc-D-Bip-OH;Fmoc-D-4,4'-Biphenylalanine;Fmoc-4-biphenyl-D-Ala;Fmoc-D-4,4'-Diphenylalanine;Fmoc-D-Bip(4,4 inverted exclamation mark )-OH;(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-phenylphenyl)propanoic Acid;Fmoc-L-4,4'-Biphenylalanine;Fmoc-D-Bip(4,4')-OH;MFCD00191199;Fmoc-D-Bph-OH;SCHEMBL3732469;Fmoc-4,4'-Biphenyl-D-alanine;DTXSID501133710;Fmoc-D-Bip(4,4atrade mark)-OH;AKOS016843705;AC-9872;CS-W011554;DS-3897;HY-W010838;(R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(biphenyl-4-yl)propanoic acid;Fmoc-D-Bip(4,4invertedexclamationmark)-OH;Fmoc-D-4,4'-biphenylalanine (Fmoc-D-Bip-OH);A879561;J-013414;N-alpha-(9-Fluorenylmethyloxycarbonyl)-D-biphenylalanine;(alphaR)-alpha-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino][1,1'-biphenyl]-4-propanoic acid;[1,1'-Biphenyl]-4-propanoic acid, alpha-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-, (alphaR)-

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

Chemical Property:

• 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:

99.3% ^*data from raw suppliers

Fmoc-d-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-d-4,4''-biphenylalanine

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

There total 8 articles about (R)-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: 20.0%

N-(9-fluorenylmethoxycarbonyl)-4-bromo-D-phenylalanine (198545-76-5,198561-04-5) + phenylboronic acid (98-80-6) → (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-([1,1'-biphenyl]-4-yl)propanoic acid (205526-38-1)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In water; isopropyl alcohol; at 40 ℃; for 20h; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.jmedchem.0c01620

upstream raw materials:

Fmoc-4-bromo-L-phenylalanine

phenylboronic acid

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

H-p-BrPhe-OH

Refernces

• 1、 Martin, Charlotte,Gimenez, Luis E.,Williams, Savannah Y.,Jing, Yu,Wu, Yiran,Hollanders, Charlie,Van Der Poorten, Olivier,Gonzalez, Simon,Van Holsbeeck, Kevin,Previti, Santo,Lamouroux, Arthur,Zhao, Suwen,Tourwé, Dirk,Stevens, Raymond C.,Cone, Roger D.,Ballet, Steven. "Structure-Based Design of Melanocortin 4 Receptor Ligands Based on the SHU-9119-hMC4R Cocrystal Structure ?". supporting information. p. 357 - 369. Retrieved 2020/12/01.
• 2、 Qiao, Jennifer X.,Fraunhoffer, Kenneth J.,Hsiao, Yi,Li, Yi-Xin,Wang, Chunlei,Wang, Tammy C.,Poss, Michael A.. "Synthesis of Fmoc-Protected Arylphenylalanines (Bip Derivatives) via Nonaqueous Suzuki-Miyaura Cross-Coupling Reactions". . p. 9499 - 9506. Retrieved 2016/10/14.