Cas no 65733-15-5 ((R)-2-Amino-3-(4-(benzyloxy)phenyl)propanoic acid)

(R)-2-Amino-3-(4-(benzyloxy)phenyl)propanoic acid is a chiral non-natural amino acid derivative featuring a benzyl-protected phenol group. Its key structural attributes include a stereocenter at the α-carbon and a benzyl ether moiety, making it valuable for peptide synthesis and medicinal chemistry applications. The (R)-enantiomer offers precise stereochemical control in the design of bioactive compounds, particularly in developing enzyme inhibitors or receptor modulators. The benzyloxy group enhances solubility in organic solvents while allowing selective deprotection for further functionalization. This compound is commonly utilized in pharmaceutical research for its role in constructing constrained peptide analogs or as a building block for targeted drug discovery. Its high purity and well-defined chirality ensure reproducibility in synthetic workflows.
(R)-2-Amino-3-(4-(benzyloxy)phenyl)propanoic acid structure
65733-15-5 structure
Product Name:(R)-2-Amino-3-(4-(benzyloxy)phenyl)propanoic acid
CAS No:65733-15-5
MF:C16H17NO3
MW:271.311084508896
CID:502204
PubChem ID:725704
Update Time:2025-05-25

(R)-2-Amino-3-(4-(benzyloxy)phenyl)propanoic acid Chemical and Physical Properties

Names and Identifiers

    • (R)-2-Amino-3-(4-(benzyloxy)phenyl)propanoic acid
    • (R)-2-AMINO-3-(4-BENZYLOXYPHENYL)PROPANOIC ACID
    • D-Tyrosine,O-(phenylmethyl)-
    • H-D-TYR (BZL)-OH
    • O-Benzyl-D-tyrosine
    • (2R)-amino-3-(4-benzyloxyphenyl)propionic acid
    • (R)-2-amino-3-(4-benzyloxyphenyl)propionic acid
    • AC1LDUUO
    • AC1Q5R0V
    • CTK8G0140
    • D-Tyr(Bzl)OH
    • H-D-Tyr(Bn)-OH
    • O-benzyl-(R)-tyrosin
    • PubChem18635
    • SureCN659105
    • H-D-TYR(BZL)-OH
    • EN300-123483
    • KAFHLONDOVSENM-OAHLLOKOSA-N
    • MFCD00077104
    • (2R)-2-amino-3-(4-phenylmethoxyphenyl)propanoic acid
    • T0XDX5TGP3
    • (2R)-2-AMINO-3-[4-(BENZYLOXY)PHENYL]PROPANOIC ACID
    • BCP14181
    • UNII-T0XDX5TGP3
    • SCHEMBL659105
    • 65733-15-5
    • (2R)-2-azaniumyl-3-(4-phenylmethoxyphenyl)propanoate
    • AKOS016843633
    • D70466
    • O-(Phenylmethyl)-D-tyrosine
    • H-D-Tyr(Bzl)
    • CS-0156174
    • O-Benzyl-D-Tyr
    • DS-5114
    • D-Tyrosine, O-(phenylmethyl)-
    • AM82338
    • MDL: H194433
    • Inchi: 1S/C16H17NO3/c17-15(16(18)19)10-12-6-8-14(9-7-12)20-11-13-4-2-1-3-5-13/h1-9,15H,10-11,17H2,(H,18,19)/t15-/m1/s1
    • InChI Key: KAFHLONDOVSENM-OAHLLOKOSA-N
    • SMILES: O(CC1C=CC=CC=1)C1C=CC(=CC=1)C[C@H](C(=O)O)N

Computed Properties

  • Exact Mass: 271.12091
  • Monoisotopic Mass: 271.12084340g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 20
  • Rotatable Bond Count: 6
  • Complexity: 294
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -0.1
  • Topological Polar Surface Area: 72.6?2

Experimental Properties

  • PSA: 72.55
  • LogP: 2.92030

(R)-2-Amino-3-(4-(benzyloxy)phenyl)propanoic acid Security Information

  • Storage Condition:Store at 0-5 ° C

(R)-2-Amino-3-(4-(benzyloxy)phenyl)propanoic acid Pricemore >>

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(R)-2-Amino-3-(4-(benzyloxy)phenyl)propanoic acid Related Literature

Additional information on (R)-2-Amino-3-(4-(benzyloxy)phenyl)propanoic acid

Professional Introduction of (R)-2-Amino-3-(4-(Benzyloxy)Phenyl)Propanoic Acid (CAS No. 65733-15-5)

The compound (R)-2-Amino-3-(4-(benzyloxy)phenyl)propanoic acid, identified by the CAS registry number 65733-15-5, is a structurally complex amino acid derivative with significant potential in various fields, including pharmaceuticals, biotechnology, and material science. This compound has garnered attention due to its unique chemical properties and promising applications in drug development and bioactive molecule synthesis.

Recent advancements in chemical synthesis have enabled researchers to explore the full potential of this compound. For instance, studies published in 2023 have highlighted its role as a key intermediate in the synthesis of bioactive molecules, particularly in the development of peptide-based drugs. The benzyloxy group attached to the phenyl ring introduces steric and electronic effects that enhance the compound's stability and bioavailability, making it an attractive candidate for drug delivery systems.

The stereochemistry of this compound, specifically the R configuration at the second carbon atom, plays a crucial role in its biological activity. Research has shown that this configuration significantly influences the compound's interaction with target proteins, thereby affecting its pharmacokinetic properties. This has led to increased interest in using this compound as a chiral building block in asymmetric synthesis.

In terms of synthesis, researchers have developed innovative methods to produce this compound with high yield and purity. For example, a 2023 study reported a one-pot synthesis involving a palladium-catalyzed cross-coupling reaction, which not only simplifies the production process but also reduces environmental impact. Such advancements underscore the importance of green chemistry principles in modern synthetic strategies.

The biological activity of (R)-2-Amino-3-(4-(benzyloxy)phenyl)propanoic acid has been extensively studied. Preclinical trials have demonstrated its potential as an anti-inflammatory agent, with studies showing significant reduction in inflammation markers in animal models. Additionally, its antioxidant properties make it a promising candidate for use in cosmetics and nutraceuticals.

From an applications perspective, this compound is being explored for its role in peptide therapeutics. Its ability to form stable amide bonds with other amino acids makes it a valuable component in peptide synthesis. Furthermore, its compatibility with solid-phase synthesis techniques has facilitated its integration into large-scale production processes.

Looking ahead, ongoing research is focused on optimizing the compound's pharmacokinetic profile to enhance its therapeutic efficacy. Collaborative efforts between academic institutions and pharmaceutical companies are paving the way for clinical trials targeting specific indications such as neurodegenerative diseases and chronic inflammatory conditions.

In conclusion, (R)-2-Amino-3-(4-(benzyloxy)phenyl)propanoic acid (CAS No. 65733-15-5) represents a versatile and promising molecule with wide-ranging applications across multiple disciplines. Its unique chemical properties, combined with recent advancements in synthesis and application techniques, position it as a key player in future innovations within the chemical and pharmaceutical industries.

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