4-BORONO-L-PHENYLALANINE

Base Information

• Chemical Name: 4-BORONO-L-PHENYLALANINE
• CAS No.: 76410-58-7
• Molecular Formula: C9H12BNO4
• Molecular Weight: 209.01
• Hs Code.: 29310099
• European Community (EC) Number: 622-791-7,807-298-9
• UNII: JSM63LV5MD
• DSSTox Substance ID: DTXSID70227242
• Nikkaji Number: J74.962A
• Wikidata: Q27281677
• ChEMBL ID: CHEMBL125582
• Mol file: 76410-58-7.mol

Synonyms:4-Borono-L-phenylalanine;L-BPA;L-p-Boronophenylalanine;4-boronophenylalanine;4-(dihydroxyboranyl)-L-phenylalanine;4-(Dihydroxyboryl)-L-phenylalanine;L-Phenylalanine, 4-borono-;p-Borono-L-phenylalanine;4-Borono-L-phenylalanine B10 enriched;

Chemical Property of 4-BORONO-L-PHENYLALANINE

Chemical Property:

• Vapor Pressure: 7.39E-09mmHg at 25°C
• Melting Point: 285-293oC (dec.)
• Refractive Index: 1.59
• Boiling Point: 449.3 °C at 760 mmHg
• PKA: 2.20±0.10(Predicted)
• Flash Point: 225.5 °C
• PSA: 103.78000
• Density: 1.34 g/cm³
• LogP: -0.97890
• Storage Temp.: 2-8°C
• Solubility.: Aqueous Acid (Slightly)
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 209.0859380
• Heavy Atom Count: 15
• Complexity: 216

Purity/Quality:

98%min ^*data from raw suppliers

4-Borono-L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)CC(C(=O)O)N)(O)O
• Isomeric SMILES: B(C1=CC=C(C=C1)C[C@@H](C(=O)O)N)(O)O
• Recent EU Clinical Trials: Boronophenylalanine (BPA)-based boron neutron capture therapy (BNCT) combined with anti-erbB1 antibody therapy in the treatment of locally recurred head and neck cancer: A phase I/II study.
• Uses: 4-Borono-L-phenylalanine is an unnatural derivative of L-Phenylalanine (P319415). a nonpolar, essential amino acid that naturally occurs in the human body and is also used to treat patients with depression. 4-Borono-L-phenylalanine is also being used as a mediator in sequential boron neutron capture therapy, a new method of treating oral cancer.

Technology Process of 4-BORONO-L-PHENYLALANINE

There total 27 articles about 4-BORONO-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: 93.2%

N-(tert-butoxycarbonyl)-4-(dihydroxyboryl)-1-phenylalanine (119771-23-2) → p-borono-L-phenylalanine (76410-58-7)

Guidance literature:

With hydrogenchloride; In water; acetone; at 55 ℃; for 1.5h;

Reference yield: 91.0%

N,N-dibenzyl-4-borono-L-phenylalanine benzyl ester (262604-05-7) → p-borono-L-phenylalanine (76410-58-7)

Guidance literature:

With hydrogenchloride; 5%-palladium/activated carbon; hydrogen; In ethanol; water; at 60 ℃; under 3750.38 - 9000.9 Torr; Reagent/catalyst; Temperature; Autoclave;

Reference yield: 67.0%

water (7732-18-5) + (4S)-3-t-butyloxycarbonyl-4-[4-(2,3-dimethyl-2,3-butanediolatoboryl)benzyl]-5-oxazolidinone (262604-04-6) → p-borono-L-phenylalanine (76410-58-7)

Guidance literature:

With sodium hydroxide; sodium periodate; sulfuric acid; In 1,4-dioxane; water; acetone; 1) NaIO4, NH4OAc, acetone/water, room temp., 48 h; 2) aq. NaOH, 1 h; 3)aq. H2SO4, 1,4-dioxane, room temp., 1 h; removal of solvent, neutralization with aq. NaOH;

DOI:10.1246/bcsj.73.231

upstream raw materials:

N-acetyl-4-dihydroxyboranyl-phenylalanine

N-(tert-butoxycarbonyl)-4-(dihydroxyboryl)-1-phenylalanine

N-benzyloxycarbonyl-4-borono-L-phenylalanine

N,N-dibenzyl-4-borono-L-phenylalanine benzyl ester

Downstream raw materials:

3-[4-(thien-3-yl)phenyl]alanine

C₁₁H₁₆BNO₄

Refernces

• 1、 -. "METHOD FOR PREPARING L-BPA". Paragraph 0123-0128. . Retrieved 2018/06/15.
• 2、 -. "Compositions, methods of preparing amino acids, and nuclear magnetic resonance spectroscopy". Page/Page column 13; sheet 3. . Retrieved 2010/11/27.