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CS-W001157 4
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2-((tert-Butoxycarbonyl)amino)-2-(naphthalen-2-yl)acetic acid

  • CAS No. 33741-79-6

  • Cat. No. CS-0186380
  • Purity≥95%
  • MDL No.None

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

2-((tert-Butoxycarbonyl)amino)-2-(naphthalen-2-yl)acetic acid|CS-0186380

Structure of 33741-79-6

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General Information

  • CAS No. 33741-79-6
  • Cat. No. CS-0186380
  • Purity ≥95%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₇H₁₉NO₄
  • Molecular Weight 301.34
  • Synonym(s) tert-Butoxycarbonylamino-phthalen-2-yl-acetic acid
  • SMILES CC(C)(OC(NC(C(O)=O)C1=CC2=CC=CC=C2C=C1)=O)C

Description

This naphthalene-containing amino acid derivative features a tert-butoxycarbonyl-protected amine and a carboxylic acid group, enabling direct incorporation into peptide synthesis. The rigid naphthyl moiety enhances structural definition, while the Boc handle ensures stability during purification and handling under standard conditions.

Application

2-((tert-Butoxycarbonyl)amino)-2-(naphthalen-2-yl)acetic acid serves as a versatile building block for peptide and heterocyclic synthesis, offering a stable, bench-ready Boc-protected amino acid with a naphthyl-containing side chain. Its functionality enables direct incorporation into solid-phase peptide synthesis and facilitates subsequent deprotection under mild acidic conditions. The naphthalene moiety provides structural rigidity and π-stacking potential, enhancing molecular recognition in target-directed design.

Synthesis

  • Route1
    • In-stock
      Di-tert-butyl dicarbonate|CS-0017817
      24424-99-5
    • 2-Amino-2-(naphthalen-2-yl)acetic acid|CS-0072662
      33741-78-5
    • ~86%
    • In-stock
      2-((tert-Butoxycarbonyl)amino)-2-(naphthalen-2-yl)acetic acid|CS-0186380
      33741-79-6

    References

    • Kukolja; Draheim; Pfeil; et al. Journal of Medicinal Chemistry, 1985 , vol. 28, # 12 p. 1886 - 1896
  • Route2
    • null|null
      1379796-45-8
    • ~%
    • In-stock
      2-((tert-Butoxycarbonyl)amino)-2-(naphthalen-2-yl)acetic acid|CS-0186380
      33741-79-6

    References

    • Baruah, Pranjal K.; Dinsmore, Jason; King, Amber M.; Salome, Christophe; De Ryck, Marc; Kaminski, Rafal; Provins, Laurent; Kohn, Harold Bioorganic and Medicinal Chemistry, 2012 , vol. 20, # 11 p. 3551 - 3564
  • Route3
    • null|null
      124-38-9
    • null|null
      1291065-86-5
    • ~%
    • In-stock
      2-((tert-Butoxycarbonyl)amino)-2-(naphthalen-2-yl)acetic acid|CS-0186380
      33741-79-6

    References

    • Mita, Tsuyoshi; Sugawara, Masumi; Hasegawa, Hiroyuki; Sato, Yoshihiro Journal of Organic Chemistry, 2012 , vol. 77, # 5 p. 2159 - 2168

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-P405-P501

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Computational Chemistry Data

  • TPSA   75.63
  • LogP   3.4902
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   3

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