26250-86-2

Basic information

• Product Name: (S)-3-benzyloxycarbonylamino-4-phenylbutyric acid
• Synonyms: (S)-3-benzyloxycarbonylamino-4-phenylbutyric acid
• CAS NO: 26250-86-2
• Molecular Weight: 313.353
• Mol File: 26250-86-2.mol
• Article Data: 22

Chemical Properties

• Melting Point: 118-119 °C
• Boiling Point: 526.7±50.0 °C(Predicted)
• Density: 1.222±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (S)-3-benzyloxycarbonylamino-4-phenylbutyric acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-benzyloxycarbonylamino-4-phenylbutyric acid(26250-86-2)
• EPA Substance Registry System: (S)-3-benzyloxycarbonylamino-4-phenylbutyric acid(26250-86-2)

Safety Data

• Hazardous Substances Data: 26250-86-2(Hazardous Substances Data)

Usage

Description

(S)-3-benzyloxycarbonylamino-4-phenylbutyric acid, also known as Boc-L-phenylalanine, is a synthetic amino acid derivative that plays a crucial role in peptide synthesis and as a substrate for proteases. It features a bulky protective group that can be removed under mild conditions, revealing the free amino group for further chemical reactions. (S)-3-benzyloxycarbonylamino-4-phenylbutyric acid is widely utilized in pharmaceutical and biochemical research, particularly for the development of new drug compounds and the study of protein structure and function. Its unique chemical properties and versatility make it a valuable tool in the field of organic and medicinal chemistry.

Uses

Used in Pharmaceutical Industry:
Boc-L-phenylalanine is used as a building block for the synthesis of various peptide-based drugs. Its ability to form stable peptides under mild conditions makes it an essential component in the development of new pharmaceutical compounds.
Used in Biochemical Research:
In the field of biochemical research, Boc-L-phenylalanine serves as a substrate for proteases, allowing scientists to study the structure and function of proteins. This understanding can lead to the discovery of novel therapeutic targets and the development of more effective drugs.
Used in Organic Chemistry:
Boc-L-phenylalanine is also utilized in organic chemistry as a versatile reagent for the synthesis of various organic compounds. Its unique chemical properties enable the formation of complex molecular structures, contributing to the advancement of organic chemistry research.

Upstream product

• 97206-05-8 methyl N-(benzyloxycarbonyl)-(3S)-3-amino-4-phenylbutanoate 
• 15196-02-8 (S)-3-[(benzyloxycarbonyl)amino]-1-diazo-4-phenyl-2-butanone 
• 15099-85-1 β-homo-(S)-phenylalanine 
• 501-53-1 benzyl chloroformate 
• 141403-49-8 (2S)-2-[N-(tert-butoxycarbonyl)amino]-3-phenyl-O-(4-methylphenylsulfonyl)propan-1-ol 
• 532-31-0 silver benzoate 
• 63-91-2 L-phenylalanine 
• 64-17-5 ethanol 
• 109453-49-8 (C₈H₇O₂)(NHCHCOO)(CH₂C₆H₅)(CO₂C₂H₅) 
• 1161-13-3 N-Cbz-L-Phe 
• 6372-14-1 N-((benzyloxy)carbonyl)-L-phenylalaninol 
• 1445444-19-8 (3S)-N-benzyloxycarbonyl-3-amino-1-nitro-4-phenylbutane 
• 187942-94-5 (3S)-N-benzyloxycarbonyl-3-amino-2-hydroxy-1-nitro-4-phenylbutane 
• 59830-60-3 benzyl (1S)-(1-formyl-2-phenylethyl)carbamate 

Downstream Products

• 15099-85-1 β-homo-(S)-phenylalanine 
• 200267-79-4 (S)-3-Benzyloxycarbonylamino-4-phenyl-butyric acid tert-butyl ester 
• 97206-05-8 methyl N-(benzyloxycarbonyl)-(3S)-3-amino-4-phenylbutanoate 
• 1616868-60-0 (S)-3-benzyloxycarbonylamino-4-phenylbutane-1-sulfonic acid 
• 819794-04-2 (S)-3-amino-4-phenylbutane-1-sulfonic acid 
• 1616868-38-2 (S)-3-(benzyloxycarbonylamino)-4-phenylbutyl methanesulfonate 
• 1443997-10-1 C₄₁H₇₃N₁₇O₈ 
• 1443997-09-8 C₄₁H₇₃N₁₇O₈ 
• 1443997-07-6 C₄₄H₇₀N₁₄O₈ 
• 1443997-06-5 C₄₄H₇₀N₁₄O₈ 
• 1443997-05-4 C₄₄H₇₀N₁₄O₈ 
• 1443997-04-3 C₄₄H₇₀N₁₂O₈ 
• 1443997-27-0 C₂₇H₃₅N₃O₇ 
• 63328-06-3 (4R)-4-amino-5-phenylpentanoic acid 

Relevant articles and documents

Synthesis of enantiopure free and N-benzyloxycarbonyl-protected 3-substituted homotaurines from naturally occurring amino acids

Enantiopure N-benzyloxycarbonyl-protected and free 3-substituted homotaurines were synthesized from naturally occurring amino acids via N-benzyloxycarbonyl protection, Arndt-Eistert homologation, reduction, esterification with thioacetic acid, and oxidation with performic acid. The current method is a convenient, practical, and salt-free method for the synthesis of enantiopure 3-substituted homotaurine with moderate to good yields.

Synthesis of enantiopure free and N-benzyloxycarbonyl-protected 3-substituted homotaurines from naturally occurring amino acids

Enantiopure N-benzyloxycarbonyl-protected and free 3-substituted homotaurines were synthesized from naturally occurring amino acids via N-benzyloxycarbonyl protection, Arndt-Eistert homologation, reduction, esterification with thioacetic acid, and oxidation with performic acid. The current method is a convenient, practical, and salt-free method for the synthesis of enantiopure 3-substituted homotaurine with moderate to good yields.

Synthesis of novel N-protected β3-amino nitriles: study of their hydrolysis involving a nitrilase-catalyzed step

Several commercially available nitrilases were investigated with regard to their potential to hydrolyze N-protected β3-amino nitriles into their corresponding N-protected β3-amino acids. The biotransformations were obtained in different proportions depending on the nitrilase involved. The best hydrolysis results were achieved for the N-Cbz-β3-amino nitrile from l-alanine using the NIT-107, in a phosphate buffer at 0.05 M. However, no biotransformation into the corresponding acids was observed for the N-sulfonylamide β3-amino nitriles. Two simple and efficient procedures to prepare the β3-amino nitriles from their analogous α-amino acids are described. Thirty four new substances were synthesized and characterized over the course of this work.