Cas no 102185-35-3 (2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acid)

2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acid is a protected amino acid derivative widely used in peptide synthesis and organic chemistry. Its key advantages include the tert-butoxycarbonyl (Boc) group, which provides excellent stability under basic conditions and selective deprotection under acidic conditions, making it suitable for orthogonal protection strategies. The sterically hindered 3,3-dimethylbutanoic acid moiety enhances solubility in organic solvents while maintaining reactivity in coupling reactions. This compound is particularly valuable in solid-phase peptide synthesis (SPPS) and medicinal chemistry, where controlled deprotection and minimal side reactions are critical. Its high purity and consistent performance ensure reliable results in complex synthetic pathways.
2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acid structure
102185-35-3 structure
Product Name:2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acid
CAS No:102185-35-3
MF:C11H21NO4
MW:231.28874373436
CID:893237
PubChem ID:5046859
Update Time:2025-06-09

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

Names and Identifiers

    • 2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acid
    • 2-(ter-butoxy carbonylamino)-3,3-dimethyl butanoic acid
    • Boc-dl-tle-oh
    • Boc-DL-α-tert-butylglycine
    • Boc-tBu-DL-Gly-OH
    • BOC-TBU-DL-GLYCINE
    • BOC-DL-GLY(TBU)-OH
    • N-Boc-DL-tert-leucine
    • Boc-DL-α-tert-butyl-Gly
    • Boc-DL-α-tert-butyl-Gly-OH
    • BOC-DL-ALPHA-T-BUTYL-GLY-OH
    • BOC-DL-ALPHA-T-BUTYLGLYCINE
    • 169870-82-0
    • AB02629
    • N-(tert-Butoxycarbonyl)-L-tert-leucine; (S)-N-Boc-2-Amino-3,3-dimethylbutyric acid
    • EN300-108892
    • 2-tert-butoxycarbonylamino-3,3-dimethyl-butyric acid
    • rac. 2-tert-butoxycarbonylamino-3,3-dimethyl-butyric acid
    • DL-2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acid
    • LRFZIPCTFBPFLX-UHFFFAOYSA-N
    • 2-tert-butoxycarbonylamino-3,3-dimethylbutyric acid
    • 2-tert.butoxycarbonylamino-3,3-dimetylbutyric acid
    • NS00005112
    • Boc-DL-alpha-tert-butylglycine
    • N-Boc-t-butylglycine
    • AB02627
    • 2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoicacid
    • N-[tert-Butoxy(hydroxy)methylidene]-3-methylvaline
    • n-boc-tert-butylglycine
    • AKOS009158949
    • AS-10048
    • 3,3-dimethyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic Acid
    • Boc-DL-alpha-tert-butyl-Gly-OH
    • BOC-(R)-2-amino-3,3-dimethylbutanoic acid
    • CS-0171674
    • DL-Valine, N-[(1,1-dimethylethoxy)carbonyl]-3-methyl-
    • 102185-35-3
    • 2-(tert-butoxycarbonylamino)-3,3-dimethylbutanoic acid
    • boc-dl-(tbu)gly-oh
    • MFCD00057782
    • Valine, N-[(1,1-dimethylethoxy)carbonyl]-3-methyl-
    • 2-tert.butoxycarbonylamino-3,3-dimethyl butyric acid
    • DTXSID00937706
    • MFCD00065575
    • boc-dl-tert-leucine
    • 2-[(TERT-BUTOXYCARBONYL)AMINO]-3,3-DIMETHYLBUTANOIC ACID
    • SCHEMBL90052
    • SY110161
    • DA-43545
    • SY021490
    • 2-{[(tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acid
    • BCP14283
    • Inchi: 1S/C11H21NO4/c1-10(2,3)7(8(13)14)12-9(15)16-11(4,5)6/h7H,1-6H3,(H,12,15)(H,13,14)
    • InChI Key: LRFZIPCTFBPFLX-UHFFFAOYSA-N
    • SMILES: O(C(NC(C(=O)O)C(C)(C)C)=O)C(C)(C)C

Computed Properties

  • Exact Mass: 231.14713
  • Monoisotopic Mass: 231.14705815g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 5
  • Complexity: 273
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2.3
  • Topological Polar Surface Area: 75.6?2

Experimental Properties

  • PSA: 75.63

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

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

Introduction to 2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acid (CAS No. 102185-35-3)

2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acid, identified by the Chemical Abstracts Service Number (CAS No.) 102185-35-3, is a specialized organic compound that has garnered significant attention in the field of pharmaceutical chemistry and biotechnology. This compound, featuring a unique structural configuration, serves as a crucial intermediate in the synthesis of various bioactive molecules. Its molecular structure incorporates a tert-butoxycarbonyl (Boc) protecting group and a 3,3-dimethylbutanoic acid backbone, which endows it with distinct chemical properties and reactivity patterns. These characteristics make it particularly valuable in the development of peptide mimetics, protease inhibitors, and other therapeutic agents.

The Boc group is a widely employed protective group in peptide synthesis, known for its stability under basic conditions and ease of removal under acidic conditions. This feature allows for precise control over the synthetic pathway, enabling chemists to construct complex peptide structures with high fidelity. The presence of the dimethyl substitution at the C3 position enhances the compound's steric hindrance, which can be strategically exploited to modulate enzyme binding affinities or improve metabolic stability in drug candidates.

In recent years, there has been a surge in research focused on developing novel inhibitors targeting various therapeutic pathways. Among these, proteases play a pivotal role in numerous biological processes, including inflammation, blood clotting, and cancer progression. 2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acid has been explored as a key building block in the design of protease inhibitors due to its ability to mimic natural substrates while incorporating pharmacophoric elements that enhance binding specificity. For instance, studies have demonstrated its utility in synthesizing inhibitors of matrix metalloproteinases (MMPs), which are implicated in tumor invasion and metastasis.

Advances in computational chemistry and molecular modeling have further accelerated the discovery of novel drug candidates derived from this compound. By leveraging high-throughput screening and structure-based drug design approaches, researchers have identified derivatives of 2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acid that exhibit potent activity against target enzymes. These derivatives often feature modifications such as altered side chains or additional functional groups designed to optimize pharmacokinetic properties and reduce off-target effects.

The pharmaceutical industry has also shown interest in this compound for its potential applications in peptide drug development. Peptide-based therapeutics are increasingly recognized for their specificity and efficacy in treating diseases such as diabetes, autoimmune disorders, and cancer. However, the inherent instability of peptides necessitates the use of protecting groups like the Boc moiety to ensure their integrity during synthesis and formulation. The structural features of 2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acid make it an ideal candidate for generating advanced peptide mimetics that can bypass some of the limitations associated with traditional peptide-based drugs.

Recent studies have highlighted the compound's role in developing next-generation biologics with improved pharmacological profiles. For example, researchers have utilized derivatives of this compound to create cyclic peptides that exhibit enhanced resistance to enzymatic degradation while maintaining biological activity. Such innovations are critical for expanding the therapeutic potential of peptide drugs and improving patient outcomes.

The synthesis of 2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acid typically involves multi-step organic reactions starting from readily available precursors. Key synthetic steps include Boc protection of an amine group followed by alkylation at the C3 position to introduce the dimethyl groups. The use of catalytic methods and green chemistry principles has further refined these synthetic routes, making them more efficient and environmentally sustainable.

In conclusion,2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acid (CAS No. 102185-35-3) represents a versatile intermediate with significant applications in pharmaceutical research and drug development. Its unique structural features and reactivity patterns make it indispensable for constructing complex bioactive molecules, particularly protease inhibitors and peptide mimetics. As research continues to uncover new therapeutic targets and innovative synthetic strategies,this compound is poised to remain at the forefront of medicinal chemistry innovation.

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