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CS-W001157 4
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BOC-(1S,3R)-3-aminocyclopentanecarboxylic acid

  • CAS No. 261165-05-3

  • Cat. No. CS-W006202
  • Purity≥95%
  • MDL No.MFCD01320857

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

BOC-(1S,3R)-3-aminocyclopentanecarboxylic acid|CS-W006202

Structure of 261165-05-3

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General Information

  • CAS No. 261165-05-3
  • Cat. No. CS-W006202
  • Purity ≥95%
  • MDL No. MFCD01320857
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₉NO₄
  • Molecular Weight 229.27
  • Synonym(s) (1S,3R)-3-[(tert-Butoxycarbonyl)amino]cyclopentanecarboxylic acid
  • SMILES O=C(O)[C@@H]1C[C@@H](CC1)NC(OC(C)(C)C)=O

Description

BOC-(1S,3R)-3-aminocyclopentanecarboxylic acid features a stereochemically defined cyclopentane scaffold with a protected amine and carboxylic acid group. This configuration enables selective incorporation into peptidomimetic architectures, where the rigid cyclopentane ring imparts conformational stability. The BOC group ensures compatibility with standard amine deprotection protocols, facilitating downstream functionalization in synthetic sequences.

Application

BOC-(1S,3R)-3-aminocyclopentanecarboxylic acid serves as a stereochemically defined building block for the synthesis of bioactive cyclopentane-containing scaffolds. The Boc group provides robust protection of the amine, enabling facile deprotection under mild acidic conditions. Its stability, compatibility with standard coupling reagents, and well-documented utility in peptide and medicinal chemistry make it ideal for constructing cyclic peptide analogs and heterocyclic intermediates.

Synthesis

  • Route1

    References

    • MERCK and CO., INC. Patent: WO2005/110409 A2, 2005 ; Location in patent: Page/Page column 30 ; WO 2005/110409 A2
  • Route2
    • Methyl (1S,3R)-3-{[(tert-butoxy)carbonyl]amino}cyclopentane-1-carboxylate|CS-0058056
      554451-12-6
    • ~%
    • In-stock
      BOC-(1S,3R)-3-aminocyclopentanecarboxylic acid|CS-W006202
      261165-05-3

    References

    • TAISHO PHARMACEUTICAL CO., LTD.; ARENA PHARMACEUTICALS, INC. Patent: WO2006/35967 A1, 2006 ; Location in patent: Page/Page column 100-101 ; WO 2006/035967 A1
  • Route3
    • Tert-butyl (1R,4S)-3-oxo-2-azabicyclo[2.2.1]Heptane-2-carboxylate|CS-0491207
      693245-53-3
    • ~%
    • In-stock
      BOC-(1S,3R)-3-aminocyclopentanecarboxylic acid|CS-W006202
      261165-05-3

    References

    • GLENMARK PHARMACEUTICALS LTD. Patent: WO2006/11035 A1, 2006 ; Location in patent: Page/Page column 26-27 ; WO 2006/011035 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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