Cas no 1207060-56-7 ((R)-2-((tert-Butoxycarbonyl)amino)-2,3-dimethylbutanoic acid)

(R)-2-((tert-Butoxycarbonyl)amino)-2,3-dimethylbutanoic acid is a chiral, Boc-protected amino acid derivative widely used in peptide synthesis and pharmaceutical research. Its sterically hindered structure, featuring a tert-butoxycarbonyl (Boc) protecting group and a dimethyl-substituted chiral center, enhances stability against racemization during coupling reactions. The Boc group allows for selective deprotection under mild acidic conditions, making it suitable for orthogonal protection strategies in complex peptide assemblies. This compound is particularly valuable in the synthesis of conformationally constrained peptides and peptidomimetics, where its rigid backbone promotes defined secondary structures. High purity and consistent performance make it a reliable building block for medicinal chemistry and bioconjugation applications.
(R)-2-((tert-Butoxycarbonyl)amino)-2,3-dimethylbutanoic acid structure
1207060-56-7 structure
Product Name:(R)-2-((tert-Butoxycarbonyl)amino)-2,3-dimethylbutanoic acid
CAS No:1207060-56-7
MF:C11H21NO4
MW:231.28900
MDL:MFCD01632039
CID:2092889
Update Time:2025-05-21

(R)-2-((tert-Butoxycarbonyl)amino)-2,3-dimethylbutanoic acid Chemical and Physical Properties

Names and Identifiers

    • (R)-2-((tert-Butoxycarbonyl)amino)-2,3-dimethylbutanoic acid
    • Boc-(R)-2-amino-2,3-dimethylbutanoic acid
    • (2S)-2,3-dimethyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid
    • (2S)-2-[(TERT-BUTOXY)CARBONYLAMINO]-2,3-DIMETHYLBUTANOIC ACID
    • (S)-2-(TERT-BUTOXYCARBONYLAMINO)-2,3-DIMETHYLBUTANOIC ACID
    • BOC-(S)-2-AMINO-2,3-DIMETHYLBUTANOIC ACID
    • MDL: MFCD01632039
    • Inchi: InChI=1S/C11H21NO4/c1-7(2)11(6,8(13)14)12-9(15)16-10(3,4)5/h7H,1-6H3,(H,12,15)(H,13,14)/t11-/m1/s1
    • InChI Key: MXPBQQXWXZWBMK-LLVKDONJSA-N
    • SMILES: CC([C@](C(O)=O)(NC(OC(C)(C)C)=O)C)C

Computed Properties

  • Exact Mass: 231.14700
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 6

Experimental Properties

  • PSA: 79.12000
  • LogP: 2.21480

(R)-2-((tert-Butoxycarbonyl)amino)-2,3-dimethylbutanoic acid Pricemore >>

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Additional information on (R)-2-((tert-Butoxycarbonyl)amino)-2,3-dimethylbutanoic acid

Recent Advances in the Application of (R)-2-((tert-Butoxycarbonyl)amino)-2,3-dimethylbutanoic Acid (CAS: 1207060-56-7) in Chemical Biology and Pharmaceutical Research

The compound (R)-2-((tert-Butoxycarbonyl)amino)-2,3-dimethylbutanoic acid (CAS: 1207060-56-7) has recently garnered significant attention in the field of chemical biology and pharmaceutical research. This chiral amino acid derivative serves as a critical building block in the synthesis of peptidomimetics and small-molecule therapeutics. Recent studies have highlighted its utility in the development of novel protease inhibitors and as a key intermediate in the synthesis of complex bioactive molecules. The tert-butoxycarbonyl (Boc) protecting group enhances its stability during synthetic processes, making it particularly valuable for multi-step organic syntheses.

In a 2023 study published in the Journal of Medicinal Chemistry, researchers utilized (R)-2-((tert-Butoxycarbonyl)amino)-2,3-dimethylbutanoic acid as a precursor for the development of selective kinase inhibitors. The study demonstrated that the steric hindrance provided by the 2,3-dimethylbutanoic acid moiety significantly improved binding affinity to target proteins while reducing off-target effects. Molecular docking simulations revealed that this compound's unique stereochemistry allows for optimal interactions with the ATP-binding pockets of specific kinases, suggesting its potential as a scaffold for next-generation targeted cancer therapies.

Another significant application was reported in Nature Chemical Biology, where this compound was employed in the synthesis of macrocyclic peptides with enhanced membrane permeability. The research team found that incorporation of (R)-2-((tert-Butoxycarbonyl)amino)-2,3-dimethylbutanoic acid at specific positions in the peptide sequence improved both metabolic stability and cellular uptake, addressing a major challenge in peptide-based drug development. These findings open new avenues for the design of orally bioavailable peptide therapeutics.

Recent synthetic methodology developments have also focused on more efficient production routes for (R)-2-((tert-Butoxycarbonyl)amino)-2,3-dimethylbutanoic acid. A 2024 publication in Organic Process Research & Development described an asymmetric catalytic hydrogenation approach that achieves >99% enantiomeric excess with significantly reduced catalyst loading compared to traditional methods. This advancement not only improves the economic viability of large-scale production but also aligns with green chemistry principles by minimizing metal waste.

In the pharmaceutical formulation space, researchers have investigated the physicochemical properties of (R)-2-((tert-Butoxycarbonyl)amino)-2,3-dimethylbutanoic acid and its derivatives. A comprehensive characterization study published in Molecular Pharmaceutics revealed exceptional solid-state stability and favorable solubility profiles in various pharmaceutical excipients, suggesting its suitability for diverse drug delivery systems. These properties are particularly valuable for developing stable formulations of poorly soluble active pharmaceutical ingredients.

Looking forward, the unique structural features of (R)-2-((tert-Butoxycarbonyl)amino)-2,3-dimethylbutanoic acid continue to inspire innovative applications in drug discovery. Current research directions include its incorporation into PROTAC (proteolysis targeting chimera) molecules and as a building block for covalent inhibitors. The compound's versatility and demonstrated biological activity profile position it as an important tool in the medicinal chemist's arsenal for addressing challenging therapeutic targets.

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