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BOC-(1R,3S)-3-aminocyclopentane carboxylic acid

  • CAS No. 161660-94-2

  • Cat. No. CS-W004812
  • Purity≥98%
  • MDL No.MFCD01320858

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

BOC-(1R,3S)-3-aminocyclopentane carboxylic acid|CS-W004812

Structure of 161660-94-2

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General Information

  • CAS No. 161660-94-2
  • Cat. No. CS-W004812
  • Purity ≥98%
  • MDL No. MFCD01320858
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₉NO₄
  • Molecular Weight 229.28
  • Synonym(s) (1S,3S)-3-[(tert-Butoxycarbonyl)amino]cyclopentanecarboxylic acid
  • SMILES OC([C@@H]1CC[C@H](NC(OC(C)(C)C)=O)C1)=O

Description

BOC-(1R,3S)-3-aminocyclopentane carboxylic acid features a stereochemically defined cyclopentane core with a protected primary amine and carboxylic acid group. This chiral building block integrates readily into peptide synthesis workflows, offering enhanced solubility and stability under standard conditions. The BOC protection enables efficient deprotection during late-stage functionalization.

Application

BOC-(1R,3S)-3-aminocyclopentane carboxylic acid serves as a stereochemically defined building block for the synthesis of cyclopentane-containing bioactive molecules. The BOC group provides robust protection of the amine, enabling selective functionalization and facilitating purification. It exhibits excellent bench stability and compatibility with standard coupling and reduction protocols, making it ideal for medicinal chemistry campaigns targeting GPCR modulators and other cyclic peptide scaffolds.

Synthesis

  • Route1

    References

    • Rodriguez-Vazquez, Nuria; Salzinger, Stephan; Silva, Luis F.; Amorin, Manuel; Granja, Juan R. European Journal of Organic Chemistry, 2013 , # 17 p. 3477 - 3493
  • Route2
    • 2-Azabicyclo[2.2.1]hept-5-en-3-one Abacavir Impurity|CS-0229666
      49805-30-3
    • ~%
    • In-stock
      BOC-(1R,3S)-3-aminocyclopentane carboxylic acid|CS-W004812
      161660-94-2

    References

    • Angewandte Chemie - International Edition, , vol. 44, # 35 p. 5710 - 5713
  • Route3

    References

    • WO2005/75426 A1, ; Page/Page column 30 ; WO 2005/075426 A1

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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