Cas no 132696-46-9 ((R)-3-(((Benzyloxy)carbonyl)amino)-2-methylpropanoic acid)

(R)-3-(((Benzyloxy)carbonyl)amino)-2-methylpropanoic acid is a chiral carboxylic acid derivative featuring a benzyloxycarbonyl (Cbz) protecting group on the amino functionality. This compound is particularly valuable in peptide synthesis and medicinal chemistry due to its stereochemical purity, as the (R)-configuration ensures precise enantioselective applications. The Cbz group offers selective deprotection under mild hydrogenolysis conditions, enhancing its utility in multi-step synthetic routes. Its methyl-substituted propanoic acid backbone contributes to steric control in coupling reactions, improving yield and selectivity. This reagent is commonly employed in the preparation of enantiomerically pure intermediates for pharmaceuticals and bioactive molecules, demonstrating high stability and compatibility with standard synthetic protocols.
(R)-3-(((Benzyloxy)carbonyl)amino)-2-methylpropanoic acid structure
132696-46-9 structure
Product Name:(R)-3-(((Benzyloxy)carbonyl)amino)-2-methylpropanoic acid
CAS No:132696-46-9
MF:C12H15NO4
MW:237.251803636551
MDL:MFCD09841919
CID:136162
PubChem ID:22865768
Update Time:2025-06-14

(R)-3-(((Benzyloxy)carbonyl)amino)-2-methylpropanoic acid Chemical and Physical Properties

Names and Identifiers

    • (R)-3-(((Benzyloxy)carbonyl)amino)-2-methylpropanoic acid
    • Cbz-R-3-Aminoisobutyric acid
    • Propanoic acid,2-methyl-3-[[(phenylmethoxy)carbonyl]amino]-, (R)- (9CI)
    • (+)-3-benzyloxycarbonylamino-2-methyl-propionic acid
    • (+)-3-Benzyloxycarbonylamino-2-methyl-propionsaeure
    • (+)-Benzyloxycarbonylamino-2-methyl-propionsaeure
    • AK-57905
    • ANW-58902
    • CTK8B7903
    • KB-209980
    • SureCN6044097
    • Cbz-(R)-3-Amino-2-methylpropanoic acid
    • Cbz-R-3-Amino isobutyric acid
    • CS-0158274
    • SCHEMBL6044097
    • DTXSID20628689
    • (2R)-2-methyl-3-(phenylmethoxycarbonylamino)propanoic acid
    • MFCD09841919
    • Propanoic acid, 2-methyl-3-[[(phenylmethoxy)carbonyl]amino]-, (R)- (9CI)
    • (R)-3-(((Benzyloxy)carbonyl)amino)-2-methylpropanoicacid
    • (2R)-3-{[(Benzyloxy)carbonyl]amino}-2-methylpropanoic acid
    • Cbz-(R)-3-Aminoisobutyric acid
    • AS-78106
    • EN300-7216837
    • AKOS016842998
    • D94483
    • 132696-46-9
    • DS-018963
    • MDL: MFCD09841919
    • Inchi: 1S/C12H15NO4/c1-9(11(14)15)7-13-12(16)17-8-10-5-3-2-4-6-10/h2-6,9H,7-8H2,1H3,(H,13,16)(H,14,15)/t9-/m1/s1
    • InChI Key: YDSJUQJHDFBDSZ-SECBINFHSA-N
    • SMILES: O(C(NC[C@H](C(=O)O)C)=O)CC1C=CC=CC=1

Computed Properties

  • Exact Mass: 237.10010796g/mol
  • Monoisotopic Mass: 237.10010796g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 7
  • Complexity: 261
  • 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: 1.5
  • Topological Polar Surface Area: 75.6?2

(R)-3-(((Benzyloxy)carbonyl)amino)-2-methylpropanoic acid Pricemore >>

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Additional information on (R)-3-(((Benzyloxy)carbonyl)amino)-2-methylpropanoic acid

Latest Research Insights on (R)-3-(((Benzyloxy)carbonyl)amino)-2-methylpropanoic acid (CAS: 132696-46-9)

The compound (R)-3-(((Benzyloxy)carbonyl)amino)-2-methylpropanoic acid (CAS: 132696-46-9) has garnered significant attention in the field of chemical biology and pharmaceutical research due to its versatile applications in peptide synthesis and drug development. Recent studies have explored its role as a key intermediate in the synthesis of chiral amino acids and bioactive peptides, highlighting its potential in the design of novel therapeutics.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the utility of (R)-3-(((Benzyloxy)carbonyl)amino)-2-methylpropanoic acid in the asymmetric synthesis of β-amino acids, which are crucial building blocks for peptidomimetics and protease inhibitors. The research team employed advanced spectroscopic techniques, including NMR and mass spectrometry, to confirm the stereochemical purity and stability of the compound under various reaction conditions.

In another groundbreaking study, researchers utilized (R)-3-(((Benzyloxy)carbonyl)amino)-2-methylpropanoic acid as a precursor for the development of targeted kinase inhibitors. The compound's chiral center and functional groups were strategically modified to enhance binding affinity and selectivity for specific kinase targets, as reported in a 2024 Nature Chemical Biology article. This work underscores the compound's potential in precision medicine and oncology drug discovery.

Recent advancements in green chemistry have also explored the sustainable synthesis of (R)-3-(((Benzyloxy)carbonyl)amino)-2-methylpropanoic acid. A 2023 ACS Sustainable Chemistry & Engineering paper detailed a biocatalytic approach using engineered enzymes, which significantly reduced the environmental footprint of the synthesis process while maintaining high enantiomeric excess (>99%).

Looking ahead, the pharmaceutical industry is increasingly interested in leveraging (R)-3-(((Benzyloxy)carbonyl)amino)-2-methylpropanoic acid for the development of next-generation peptide-based therapeutics. Its unique structural features make it an attractive candidate for addressing challenges in drug delivery and bioavailability, particularly for central nervous system targets.

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