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CS-W001157 4
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(S)-2-((tert-Butoxycarbonyl)amino)-3-(naphthalen-1-yl)propanoic acid

  • CAS No. 55447-00-2

  • Cat. No. CS-W009913
  • Purity≥98%
  • MDL No.MFCD00085377

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

(S)-2-((tert-Butoxycarbonyl)amino)-3-(naphthalen-1-yl)propanoic acid|CS-W009913

Structure of 55447-00-2

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General Information

  • CAS No. 55447-00-2
  • Cat. No. CS-W009913
  • Purity ≥98%
  • MDL No. MFCD00085377
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₈H₂₁NO₄
  • Molecular Weight 315.36
  • Synonym(s) None
  • SMILES CC(C)(OC(N[C@H](C(O)=O)CC1=CC=CC2=CC=CC=C21)=O)C

Description

This chiral building block features a protected (S)-amino acid scaffold with a naphthalen-1-yl substituent, enabling direct incorporation into peptide sequences. The tert-butoxycarbonyl group provides stability and facilitates selective deprotection during synthesis.

Application

(S)-2-((tert-Butoxycarbonyl)amino)-3-(naphthalen-1-yl)propanoic acid serves as a key chiral building block for peptide and heterocyclic synthesis. The Boc-protected amine enables orthogonal functional group manipulation, while the naphthalene moiety provides a rigid aromatic scaffold. This compound exhibits excellent bench stability, facilitates straightforward purification, and participates reliably in standard coupling reactions, making it well-suited for medicinal chemistry campaigns requiring defined stereochemistry and structural complexity.

Synthesis

  • Route1

    References

    • Rodriguez; Bernad; Galas; Lignon; Laur; Aumelas; Martinez European Journal of Medicinal Chemistry, 1991 , vol. 26, # 3 p. 245 - 253
  • Route2
    • null|null
      148745-10-2
    • ~70%
    • In-stock
      (S)-2-((tert-Butoxycarbonyl)amino)-3-(naphthalen-1-yl)propanoic acid|CS-W009913
      55447-00-2

    References

    • Medina; Moyano; Pericas; Riera Journal of Organic Chemistry, 1998 , vol. 63, # 23 p. 8574 - 8578
  • Route3
    • null|null
      192125-28-3
    • ~%
    • In-stock
      (S)-2-((tert-Butoxycarbonyl)amino)-3-(naphthalen-1-yl)propanoic acid|CS-W009913
      55447-00-2

    References

    • Journal of Organic Chemistry, , vol. 63, # 23 p. 8574 - 8578

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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   75.63
  • LogP   3.3602
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   4

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