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CS-W001157 4
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(1R,3S)-Cyclopentane-1,3-dicarboxylic acid

  • CAS No. 876-05-1

  • Cat. No. CS-0070727
  • Purity≥97%
  • MDL No.None

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

(1R,3S)-Cyclopentane-1,3-dicarboxylic acid|CS-0070727

Structure of 876-05-1

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General Information

  • CAS No. 876-05-1
  • Cat. No. CS-0070727
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₁₀O₄
  • Molecular Weight 158.15
  • Synonym(s) cis-1,3-Cyclopentanedicarboxylic acid
  • SMILES O=C(O)[C@@H](CC1)C[C@@H]1C(O)=O

Description

This chiral cyclopentane-1,3-dicarboxylic acid features a rigid, cis-configured scaffold ideal for probing stereochemical effects in medicinal chemistry. The proximal carboxylate groups enable straightforward derivatization and coordination in metal-ligand systems. Bench-stable and moisture-tolerant, it integrates seamlessly into synthetic routes requiring defined spatial orientation.

Application

(1R,3S)-Cyclopentane-1,3-dicarboxylic acid serves as a valuable chiral building block in the synthesis of bioactive molecules and natural product analogs. Its defined stereochemistry enables predictable stereoselective transformations, while the dicarboxylic acid functionality offers versatile handles for derivatization, including esterification, amide formation, and metal coordination. The compound exhibits excellent bench stability and facilitates efficient purification via recrystallization or chromatography, making it well-suited for use in medicinal chemistry campaigns and catalyst development.

Synthesis

  • Route1

    References

    • Carmen Balo; Fernandez, Franco; Lens, Evangelina; Lopez, Carmen; De Clercq, Erik; Andrei, Graciela; Snoeck, Robert; Baizarini, Jan Nucleosides and Nucleotides, 1996 , vol. 15, # 7-8 p. 1335 - 1346
  • Route2
    • null|null
      16329-23-0
    • ~69%
    • In-stock
      (1R,3S)-Cyclopentane-1,3-dicarboxylic acid|CS-0070727
      876-05-1

    References

    • Ruholl, Heinrich; Schaefer, Hans J. Synthesis, 1988 , # 1 p. 54 - 56
  • Route3
    • Bicyclo[2.2.1]heptane-2,3-diol|CS-0875647
      14440-78-9
    • ~42%
    • In-stock
      (1R,3S)-Cyclopentane-1,3-dicarboxylic acid|CS-0070727
      876-05-1

    References

    • Taylor, Jay E. Synthesis, 1985 , # 12 p. 1142 - 1144

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   74.6
  • LogP   0.5719
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   2

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