Cas no 69541-68-0 ((R)-2-((tert-butoxycarbonyl)amino)-3-(1-tosyl-1H-imidazol-4-yl)propanoic acid)

(R)-2-((tert-Butoxycarbonyl)amino)-3-(1-tosyl-1H-imidazol-4-yl)propanoic acid is a chiral amino acid derivative featuring a tert-butoxycarbonyl (Boc) protecting group and a tosyl-protected imidazole side chain. This compound is particularly valuable in peptide synthesis and medicinal chemistry due to its ability to introduce imidazole functionality while maintaining stereochemical integrity. The Boc group ensures selective deprotection under mild acidic conditions, facilitating further modifications. The tosyl group enhances stability during synthetic procedures. Its structural features make it a versatile intermediate for designing bioactive molecules, including enzyme inhibitors and receptor modulators. High purity and well-defined chirality ensure reproducibility in research applications. Suitable for use in solid-phase peptide synthesis and as a building block for complex heterocyclic systems.
(R)-2-((tert-butoxycarbonyl)amino)-3-(1-tosyl-1H-imidazol-4-yl)propanoic acid structure
69541-68-0 structure
Product Name:(R)-2-((tert-butoxycarbonyl)amino)-3-(1-tosyl-1H-imidazol-4-yl)propanoic acid
CAS No:69541-68-0
MF:C18H23N3O6S
MW:409.456723451614
MDL:MFCD00037890
CID:58984
PubChem ID:40418673
Update Time:2025-08-04

(R)-2-((tert-butoxycarbonyl)amino)-3-(1-tosyl-1H-imidazol-4-yl)propanoic acid Chemical and Physical Properties

Names and Identifiers

    • N-Boc-N'-tosyl-D-histidine
    • Boc-D-His(Tos)-OH
    • N-tert-Butyloxycarbonyl-N'-tosyl-D-histidine
    • Boc-D-His(1-Tos)-OH
    • Boc-D-His(Tos)
    • Boc-Nim-Tosyl-D-Histidine
    • Boc-D-His(tau-Tos)-OH
    • Boc-D-His(t-Tos)-OH
    • BOC-D-HISTIDINE(TOS)-OH
    • N-Boc-N'-tosyl-D-his
    • (R)-2-((tert-butoxycarbonyl)amino)-3-(1-tosyl-1H-imidazol-4-yl)propanoic acid
    • AKOS015842538
    • (R)-2-(tert-butoxycarbonylamino)-3-(1-tosyl-1H-imidazol-4-yl)propanoic acid
    • M06184
    • 69541-68-0
    • AC-8620
    • N-[(1,1-Dimethylethoxy)carbonyl]-1-[(4-methylphenyl)sulfonyl]-D-histidine
    • N-alpha-t-Butyloxycarbonyl-N-im-t-tosyl-D-histidine (Boc-D-His(Tos)-OH)
    • DTXSID901146981
    • Q-101828
    • FD21728
    • AC-8619
    • (2R)-3-[1-(4-methylphenyl)sulfonylimidazol-4-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
    • S-69541-68-0
    • CS-0187329
    • n-boc-1-(p-toluenesulfonyl)-d-histidine
    • J-300151
    • AKOS015895739
    • MFCD00037890
    • AS-49184
    • D-Histidine,N-[(1,1-dimethylethoxy)carbonyl]-1-[(4-methylphenyl)sulfonyl]-
    • (2R)-2-[(TERT-BUTOXYCARBONYL)AMINO]-3-[1-(4-METHYLBENZENESULFONYL)IMIDAZOL-4-YL]PROPANOIC ACID
    • (2R)-2-[(tert-butoxycarbonyl)amino]-3-{1-[(4-methylphenyl)sulfonyl]-1H-imidazol-4-yl}propanoic acid
    • MDL: MFCD00037890
    • Inchi: 1S/C18H23N3O6S/c1-12-5-7-14(8-6-12)28(25,26)21-10-13(19-11-21)9-15(16(22)23)20-17(24)27-18(2,3)4/h5-8,10-11,15H,9H2,1-4H3,(H,20,24)(H,22,23)/t15-/m1/s1
    • InChI Key: DCLJSEPKYJSEHW-OAHLLOKOSA-N
    • SMILES: S(C1C=CC(C)=CC=1)(N1C=NC(=C1)C[C@H](C(=O)O)NC(=O)OC(C)(C)C)(=O)=O

Computed Properties

  • Exact Mass: 409.13100
  • Monoisotopic Mass: 409.131
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 9
  • Heavy Atom Count: 28
  • Rotatable Bond Count: 9
  • Complexity: 662
  • 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
  • Topological Polar Surface Area: 136A^2
  • XLogP3: 2.2

Experimental Properties

  • Density: 1.33
  • PSA: 135.97000
  • LogP: 3.42060

(R)-2-((tert-butoxycarbonyl)amino)-3-(1-tosyl-1H-imidazol-4-yl)propanoic acid Security Information

  • Storage Condition:-15°C

(R)-2-((tert-butoxycarbonyl)amino)-3-(1-tosyl-1H-imidazol-4-yl)propanoic acid Pricemore >>

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Additional information on (R)-2-((tert-butoxycarbonyl)amino)-3-(1-tosyl-1H-imidazol-4-yl)propanoic acid

Introduction to (R)-2-((tert-butoxycarbonyl)amino)-3-(1-tosyl-1H-imidazol-4-yl)propanoic Acid and Its Applications in Modern Chemical Biology

(R)-2-((tert-butoxycarbonyl)amino)-3-(1-tosyl-1H-imidazol-4-yl)propanoic acid, with the CAS number 69541-68-0, is a sophisticated organic compound that has garnered significant attention in the field of chemical biology and pharmaceutical research. This compound, characterized by its chiral center and functional groups, serves as a crucial intermediate in the synthesis of various bioactive molecules. Its unique structural features make it particularly valuable in the development of novel therapeutic agents targeting a wide range of biological pathways.

The< strong>tert-butoxycarbonyl (Boc) group attached to the amino functionality provides stability and protection during synthetic procedures, allowing for selective modifications at other positions. This characteristic is especially beneficial in multi-step syntheses where regioselectivity is paramount. Additionally, the presence of a< strong>tosyl (Ts) group on the imidazole ring enhances the compound's solubility and reactivity, making it an ideal candidate for further derivatization.

In recent years, there has been a surge in research focused on the development of chiral auxiliaries and ligands for asymmetric synthesis. The< strong>(R)-configuration of this compound makes it a valuable tool in constructing enantiomerically pure molecules, which are often essential for achieving desired pharmacological effects. The growing interest in< strong>imidazole derivatives as pharmacophores further underscores the importance of this compound in medicinal chemistry.

One of the most compelling applications of (R)-2-((tert-butoxycarbonyl)amino)-3-(1-tosyl-1H-imidazol-4-yl)propanoic acid is in the synthesis of protease inhibitors. Proteases play a critical role in numerous biological processes, and their inhibition is a key strategy in drug development. The imidazole moiety can interact with the active sites of these enzymes, while the Boc-protected amino group allows for controlled modifications. Recent studies have demonstrated its utility in developing inhibitors targeting diseases such as cancer and inflammation.

The compound's versatility extends to its use as a building block for peptidomimetics. Peptidomimetics are designed to mimic the bioactivity of natural peptides but with improved stability and pharmacokinetic properties. The combination of< strong>Boc-amino and< strong/tosyl-imidazole functionalities provides a scaffold that can be easily modified to create diverse libraries of compounds for high-throughput screening.

Advances in computational chemistry have also highlighted the potential of (R)-2-((tert-butoxycarbonyl)amino)-3-(1-tosyl-1H-imidazol-4-yl)propanoic acid in rational drug design. Molecular modeling studies have shown that its structure can be optimized to enhance binding affinity to target proteins. This has led to innovative approaches in designing next-generation drugs with improved efficacy and reduced side effects.

The role of this compound in drug discovery is further underscored by its presence in several clinical trials targeting neurological disorders. The ability to fine-tune its structure allows researchers to develop molecules that interact selectively with specific neural receptors. Preliminary results from these trials are promising, indicating that derivatives of this compound may offer significant therapeutic benefits.

In conclusion, (R)-2-((tert-butoxycarbonyl)amino)-3-(1-tosyl-1H-imidazol-4-yl)propanoic acid (CAS no 69541-68-0) is a multifaceted compound with broad applications in chemical biology and pharmaceutical research. Its unique structural features make it an invaluable tool for synthesizing bioactive molecules, particularly protease inhibitors and peptidomimetics. As research continues to uncover new therapeutic targets and methodologies, this compound is poised to play an even greater role in the development of innovative treatments for various diseases.

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