147923-08-8

Basic information

• Product Name: BOC-L-4,4'-BIPHENYLALANINE
• Synonyms: 3-(4-BIPHENYLYL)-N-(T-BUTOXYCARBONYL)-L-ALANINE;3-(4-BIPHENYLYL)-N-(TERT-BUTOXYCARBONYL)-L-ALANINE;(S)-2-(BOC-AMINO)-3-(4-BIPHENYLYL)PROPIONIC ACID;(S)-3-BIPHENYL-4-YL-2-TERT-BUTOXYCARBONYLAMINO-PROPIONIC ACID;(S)-N-ALPHA-T-BUTYLOXYCARBONYL-BIPHENYLALANINE;N-ALPHA-T-BUTOXYCARBONYL-L-(4-PHENYL)PHENYLALANINE;N-ALPHA-TERT-BUTYLOXYCARBONYL-L-BIPHENYLALANINE;N-ALPHA-T-BUTOXYCARBONYL-4,4'-BIPHENYL-L-ALANINE
• CAS NO: 147923-08-8
• Molecular Formula: C₂₀H₂₃NO₄
• Molecular Weight: 341.4
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;Biphenyl & Diphenyl ether;Amino Acid Derivatives;a-amino
• Mol File: 147923-08-8.mol
• Article Data: 12

Chemical Properties

• Melting Point: 103-107 °C(lit.)
• Boiling Point: 528.2 °C at 760 mmHg
• Flash Point: 273.2 °C
• Appearance: /
• Density: 1.161 g/cm³
• Vapor Pressure: 2.33E-12mmHg at 25°C
• Refractive Index: 1.555
• Storage Temp.: Store at RT.
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 3.88±0.10(Predicted)
• CAS DataBase Reference: BOC-L-4,4'-BIPHENYLALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-L-4,4'-BIPHENYLALANINE(147923-08-8)
• EPA Substance Registry System: BOC-L-4,4'-BIPHENYLALANINE(147923-08-8)

Safety Data

• Hazard Codes: N,Xi,Xn
• Statements: 50/53-41-38-20/22-63
• Safety Statements: 60-61-36-26-36/37
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 147923-08-8(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

N-Boc-4-phenyl-L-phenylalanine is a reactant used in the synthesis of novel phenylalanines derived diamides as factor XIa inhibitors used in the treatment.

InChI:InChI=1/C21H25NO4/c1-21(2,3)26-20(25)22-18(19(24)14-23)13-15-9-11-17(12-10-15)16-7-5-4-6-8-16/h4-12,18,23H,13-14H2,1-3H3,(H,22,25)

Upstream product

• 137255-86-8 methyl (S)-3-([1,1'-biphenyl]-4-yl)-2-((tert-butoxycarbonyl)amino)propanoate 
• 103882-09-3 N-Boc-4-I-Phe-OH 
• 24424-99-5 di-tert-butyl dicarbonate 
• 155760-02-4 (S)-3-([1,1'-biphenyl]-4-yl)-2-aminopropanoic acid 
• 266306-18-7 (S)-3-(4-Bromo-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester 
• 98-80-6 phenylboronic acid 
• 62129-39-9 4-bromo-N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-phenylalanine 
• 1200-07-3 3-(4-bromophenyl)acrylic acid 
• 24250-84-8 H-p-BrPhe-OH 

Downstream Products

• 200864-90-0 [(S)-2-Biphenyl-4-yl-1-((S)-1-phenyl-ethylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester 
• 200864-88-6 {(S)-2-Biphenyl-4-yl-1-[2-(4-hydroxy-phenyl)-ethylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester 
• 200864-86-4 [(S)-2-Biphenyl-4-yl-1-(3-morpholin-4-yl-propylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester 
• 155873-50-0 (S)--β-alanine benzyl ester 
• 1026595-70-9 {(S)-1-[(S)-1-((S)-1-Benzyl-3-chloro-2-oxo-propylcarbamoyl)-2-carbamoyl-ethylcarbamoyl]-2-biphenyl-4-yl-ethyl}-carbamic acid tert-butyl ester 
• 153037-45-7 benzyl (2S)-2-[[(tert-butoxy)carbonyl]amino]-3-(4-phenylphenyl)propanoate 

Relevant articles and documents

A self-assembling NHC-PD-loaded calixarene as a potent catalyst for the Suzuki-Miyaura cross-coupling reaction in water

Nanoformulated calix[8]arenes functionalized with N-heterocyclic carbene (NHC)palladium complexes were found to be efficient nano-reactors for Suzuki-Miyaura cross-coupling reactions of water soluble iodo- and bromoaryl compounds with cyclic triol arylborates at low temperature in water without any organic co-solvent. Combined with an improved one-step synthesis of triol arylborates from boronic acid, this remarkably efficient new tool provided a variety of 40-arylated phenylalanines and tyrosines in good yields at low catalyst loading with a wide functional group tolerance.

Tertiary-butoxycarbonyl (Boc) – A strategic group for N-protection/deprotection in the synthesis of various natural/unnatural N-unprotected aminoacid cyanomethyl esters

A number of cyanomethyl esters of natural/unnatural aminoacids with un-protected amino functionality were synthesized because of their synthetic and medicinal importance. Critical N-Boc deprotection methods in the presence of labile (hydrolytic sensitivity) cyanomethyl functionality were screened thoroughly and it was found that readily available 4M HCl in 1,4-dioxane solution (2–4 equiv); acetonitrile, 0 °C, 2–4 h was a suitable condition. This condition was generalized and successfully applied to a variety of alkyl, alkynyl, aryl, heteroaryl, benzyl, azido, spiro amino acid cyanomethylesters irrespective of the nature of the amine (primary or secondary) and the distance between the amine and ester group to achieve final deprotected amino esters with high yield, and purity compared to other commonly known N-protecting groups (Cbz, Fmoc, Ac, Bn, Bz etc.). It was also demonstrated that N-Boc protected aminoacid cyanomethylesters are stable enough to carry out further functionalization compared to N-unprotected counterparts.

PLGA-PEG-supported Pd nanoparticles as efficient catalysts for Suzuki-Miyaura coupling reactions in water

Chemical transformations that can be performed selectively under physiological conditions are highly desirable tools to track biomolecules and manipulate complex biological processes. Here, we report a new nanocatalyst consisting of small palladium nanoparticles stabilized on the surface of PLGA-PEG nanoparticles that show excellent catalytic activity for the modification of biological building blocks through Suzuki-Miyaura cross-coupling reactions in water. Brominated or iodinated amino acids were coupled with aryl boronic acids in phosphate buffer in good yields. Interestingly, up to 98% conversion into the coupled amino acid could be achieved in 2 h at 37°C using the stable, water-soluble cyclic triolborate as organometallic partner in the presence of only 1 mol% of palladium. These results pave the way for the modification of biomolecules in complex biological systems such as the intracellular space.