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CS-W001157 4
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3-{Benzyl[(tert-butoxy)carbonyl]amino}propanoic acid

  • CAS No. 289889-03-8

  • Cat. No. CS-0124679
  • Purity≥98%
  • MDL No.MFCD04037900

*For research and further manufacturing use only, not for direct human use.

3-{Benzyl[(tert-butoxy)carbonyl]amino}propanoic acid|CS-0124679

Structure of 289889-03-8

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General Information

  • CAS No. 289889-03-8
  • Cat. No. CS-0124679
  • Purity ≥98%
  • MDL No. MFCD04037900
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₂₁NO₄
  • Molecular Weight 279.33
  • Synonym(s) 3-[Benzyl(tert-butoxycarbonyl)amino]propanoic acid
  • SMILES O=C(O)CCN(CC1=CC=CC=C1)C(OC(C)(C)C)=O

Description

This protected amino acid derivative features a benzylated amine group flanked by a tert-butoxycarbonyl (Boc) protecting group and a carboxylic acid terminus. Designed for peptide synthesis, it integrates seamlessly into solid-phase workflows, offering stable handling and selective deprotection under mild acidic conditions.

Application

3-{Benzyl[(tert-butoxy)carbonyl]amino}propanoic acid serves as a versatile building block for the synthesis of bioactive peptides and heterocyclic scaffolds. The Boc-protected amino group enables orthogonal handling in multi-step syntheses, while the pendant benzyl moiety offers structural rigidity and potential for further functionalization. This compound exhibits excellent bench stability, facilitates straightforward purification via standard chromatographic methods, and participates reliably in amide coupling and reduction reactions within established peptide chemistry workflows.

Synthesis

  • Route1
    • null|null
      153749-96-3
    • ~99%
    • In-stock
      3-{Benzyl[(tert-butoxy)carbonyl]amino}propanoic acid|CS-0124679
      289889-03-8

    References

    • Actelion Pharmaceuticals Ltd. Patent: US2009/62342 A1, 2009 ; Location in patent: Page/Page column 14 ;
  • Route2
    • null|null
      98014-76-7
    • ~%
    • In-stock
      3-{Benzyl[(tert-butoxy)carbonyl]amino}propanoic acid|CS-0124679
      289889-03-8

    References

    • De Michelis; Rocheblave; Priem; Chermann; Kraus Bioorganic and Medicinal Chemistry, 2000 , vol. 8, # 6 p. 1253 - 1262
  • Route3
    • Methyl 3-(benzyl(tert-butoxycarbonyl)amino)propanoate|CS-0719600
      155339-52-9
    • ~%
    • In-stock
      3-{Benzyl[(tert-butoxy)carbonyl]amino}propanoic acid|CS-0124679
      289889-03-8

    References

    • Zerovnik, Darja; Groselj, Uros; Kralj, David; Malavasic, Crt; Bezensek, Jure; Dahmann, Georg; Stare, Katarina; Meden, Anton; Stanovnik, Branko; Svete, Jurij Synthesis, 2010 , # 19 art. no. T09210SS, p. 3363 - 3373

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   66.84
  • LogP   2.8984
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   5

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