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CS-W001157 4
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(1S,2S)-2-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid

  • CAS No. 143679-80-5

  • Cat. No. CS-0040738
  • Purity≥97%
  • MDL No.None

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

(1S,2S)-2-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid|CS-0040738

Structure of 143679-80-5

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General Information

  • CAS No. 143679-80-5
  • Cat. No. CS-0040738
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₉NO₄
  • Molecular Weight 229.27
  • Synonym(s) (1S,2S)-Boc-aminocyclopentanecarboxylic acid
  • SMILES O=C([C@@H]1[C@@H](NC(OC(C)(C)C)=O)CCC1)O

Description

This chiral cyclopentane derivative features a protected amine and carboxylic acid group, enabling direct incorporation into peptide synthesis. The tert-butoxycarbonyl (Boc) moiety provides stability during reaction sequences, while the (1S,2S) stereochemistry ensures high diastereoselectivity in downstream coupling steps.

Application

(1S,2S)-2-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid serves as a stereochemically defined building block for cyclopentane-based peptidomimetics and bioactive scaffolds. The Boc-protected amine enables straightforward functionalization and orthogonal deprotection, while the carboxylic acid supports coupling reactions with minimal epimerization. Its bench-stable, crystalline nature facilitates handling and purification in multi-step syntheses.

Synthesis

  • Route1
    • ethyl (1S,2S)-2-((tert-butoxycarbonyl)amino)cyclopentane-1-carboxylate|CS-0775476
      143617-95-2
    • ~84%
    • In-stock
      (1S,2S)-2-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid|CS-0040738
      143679-80-5

    References

    • Tilley, Jefferson W.; Danho, Waleed; Shiuey, Shian-Jun; Kulesha, Irina; Swistok, Joseph; et al. Journal of Medicinal Chemistry, 1992 , vol. 35, # 21 p. 3774 - 3783
  • Route2

    References

    • Journal of the American Chemical Society, , vol. 126, # 46 p. 15067 - 15073
  • Route3
    • (1s,2s)-2-(((s)-1-Phenylethyl)amino)cyclopentane-1-carboxylic acid|CS-0663716
      359586-68-8
    • ~%
    • In-stock
      (1S,2S)-2-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid|CS-0040738
      143679-80-5

    References

    • Journal of the American Chemical Society, , vol. 126, # 46 p. 15067 - 15073

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

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Computational Chemistry Data

  • TPSA   75.63
  • LogP   1.7644
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   2

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