77119-84-7

Basic information

• Product Name: BOC-D-PHE-OME
• Synonyms: BOC-D-PHE-OME;BOC-D-PHENYLALANINE METHYL ESTER;N-ALPHA-T-BUTOXYCARBONYL-D-PHENYLALANINE METHYL ESTER;N-Boc-(D)-Phenylalanine methyl ester;N-tert-Butoxycarbonyl-D-phenylalanine methyl ester;(R)-Methyl 2-((tert-butoxycarbonyl)amino)-3-phenylpropanoate;-3-phenylpropanoate
• CAS NO: 77119-84-7
• Molecular Formula: C₁₅H₂₁NO₄
• Molecular Weight: 279.33
• EINECS: 205-525-8
• Mol File: 77119-84-7.mol
• Article Data: 62

Chemical Properties

• Melting Point: 51 °C
• Boiling Point: 403.7±38.0 °C(Predicted)
• Appearance: /Solid
• Density: 1.099±0.06 g/cm3(Predicted)
• Storage Temp.: Store at 0-5°C
• PKA: 11.17±0.46(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: BOC-D-PHE-OME(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-D-PHE-OME(77119-84-7)
• EPA Substance Registry System: BOC-D-PHE-OME(77119-84-7)

Safety Data

• Hazardous Substances Data: 77119-84-7(Hazardous Substances Data)

Usage

Description

BOC-D-PHE-OME, also known as N-Boc-D-phenylalanine methyl ester, is a chiral compound that serves as an essential intermediate in the synthesis of various pharmaceuticals and bioactive molecules. Its unique structure, featuring a protected D-phenylalanine residue and a methyl ester group, makes it a versatile building block in organic chemistry and drug development.

Uses

Used in Pharmaceutical Industry:
BOC-D-PHE-OME is used as a primary and secondary intermediate in chemical research for the development of new pharmaceuticals and bioactive compounds. Its chiral nature and protected functional groups allow for selective reactions and the synthesis of complex molecules with potential therapeutic applications.
Used in Organic Chemistry Research:
In the field of organic chemistry, BOC-D-PHE-OME serves as a valuable intermediate for the synthesis of various organic compounds. Its protected amino acid structure enables chemists to carry out reactions with high selectivity, facilitating the preparation of enantiomerically pure compounds for use in biological and medicinal studies.
Used in Peptide Synthesis:
BOC-D-PHE-OME is also employed in the synthesis of peptides and peptidomimetics, where its protected amino acid structure allows for the stepwise assembly of peptide chains with controlled stereochemistry. This is particularly important in the development of peptide-based drugs and vaccines, where the stereochemistry of the peptide backbone can significantly influence biological activity.
Overall, BOC-D-PHE-OME is a versatile and valuable intermediate in the fields of pharmaceuticals, organic chemistry, and peptide synthesis, playing a crucial role in the development of new drugs, bioactive molecules, and materials with potential applications in medicine and other industries.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 15028-44-1 DL-phenylalanine methyl ester 
• 31954-27-5 N-(tert-butoxycarbonyl)glycine methyl ester 
• 108-88-3 toluene 
• 50877-94-6 methyl 2-(N-hydroxyimino)-3-phenylpropanoate 
• 4530-18-1 2-(tert-butoxycarbonylamino)-3-phenylpropionic acid 
• 74-88-4 methyl iodide 
• 18942-49-9 Boc-D-Phe-OH 
• 77-78-1 dimethyl sulfate 
• 51987-73-6 methyl 2-tert-butoxycarbonylamino-3-phenylpropanoate 
• 616-38-6 carbonic acid dimethyl ester 
• 55477-80-0 methyl 2-[(tert-butoxycarbonyl)amino]acrylate 
• 98-80-6 phenylboronic acid 
• 100-52-7 benzaldehyde 

Downstream Products

• 154345-84-3 (D,L)-3-(2-furyl)-5-(2-phenyl-1-tert-butyloxycarbonylaminoethyl)-1,2,4-oxadiazole 
• 919529-35-4 tert-butyl (R)-(1-hydrazinyl-1-oxo-3-phenylpropan-2-yl)carbamate 
• 1005324-46-8 tert-butyl (2R, 3S)-3-hydroxy-4-(N-isobutyl-4-nitrophenylsulfonamido)-1-phenylbutan-2-ylcarbamate 
• 1402142-62-4 4-amino-N-((2S,3R)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide 
• 1402142-63-5 (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (2R,3S)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl carbamate 
• 1005324-40-2 C₁₉H₃₂N₂O₃ 
• 923601-69-8 (1R,2S)[3-chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid 1,1-dimethylethyl ester 
• 156474-21-4 tert-butyl [(2R,3R)]-(-)-(1-oxiranyl-2-phenylethyl)carbamate 
• 150935-37-8 (R)-(1-benzyl-3-chloro-2-oxopropyl)carbamic acid t-butyl ester 
• 1400634-55-0 C₂₇H₃₀N₂O₄ 
• 1371568-31-8 (1-benzyl-2-hex-1-ynyl-2-hydroxy-oct-3-ynyl)carbamic acid tert-butyl ester 
• 1429939-15-0 2-benzyl-5-butyl-3-hex-1-ynyl-pyrrole-1-carboxylic acid tert-butyl ester 
• 1395472-67-9 (1-benzyl-2-hydroxy-4-phenyl-2-(phenylethynyl)-but-3-ynyl)carbamic acid tert-butyl ester 
• 1429939-12-7 2-benzyl-5-phenyl-3-phenylethynyl-pyrrole-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Asymmetric Reduction of Aromatic α-Dehydroamino Acid Esters with Water as Hydrogen Source

The asymmetric reduction of aromatic α-dehydroamino acid esters with water as the hydrogen source was developed by a Rh/Cu co-catalytic system. The reaction tolerates various functional groups, providing a valuable synthetic tool to access chiral α-amino acid esters readily. Moreover, the present methodology also was applied in the cost-effective and easy to handle preparation of chiral deuterated α-amino esters by using D2O.

Synthesis and photophysics of benzazole based triazoles with amino acid-derived pendant units. Multiparametric optical sensors for BSA and CT-DNA in solution

Herein we report the synthesis of a series of amino acid-derived triazoles by an organocatalytic cycloaddition reaction between azides and carbonyl compounds, catalyzed by a simple amine. These compounds present absorption maxima located in the UV-B ascribed to fully spin and symmetry allowed electronic transitions and a main fluorescence emission in the UV-A (~380 nm) with a relatively large Stokes shift (5700 cm?1). No significant solvatochromism was observed in both ground and excited states. Unexpectedly, the benzoxazole derivatives presented much higher fluorescence quantum yield values (40–80%) of compared to the sulfur analogues (3–6%). In addition, the DNA binding assays indicated that these compounds presented strong interaction with CT-DNA, which could be attributed to π-stacking and intermolecular hydrogen-bonding. The interaction of the benzazoles with bovine serum albumin (BSA) was also investigated, where a suppression mechanism was observed. In each case, docking was performed to better understand the observed interactions.

Asymmetric Synthesis of Functionalized Phenylalanine Derivatives via Rh-Catalyzed Conjugate Addition and Enantioselective Protonation Cascade

The asymmetric conjugate addition of arylboronic acids to N-phthalimidodehydroalanine 1i catalyzed by Rh(I)/L1a enables the facile preparation of chiral functionalized phenylalanines. The reaction proceeds by a conjugate addition and enantioselective protonation cascade, affording a rhodium enolate that undergoes re-face protonation. The reaction tolerates various arylboronic acids and can be used in the gram-scale synthesis of (S)-phenylalanine hydrochloride, demonstrating the reaction scope and the synthetic feasibility of the process.