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CS-W001157 4
Total: USD 88.00

(S)-Tetrahydrofuran-3-carboxylic acid

  • CAS No. 168395-26-4

  • Cat. No. CS-0053249
  • Purity≥97%
  • MDL No.None

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

(S)-Tetrahydrofuran-3-carboxylic acid|CS-0053249

Structure of 168395-26-4

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General Information

  • CAS No. 168395-26-4
  • Cat. No. CS-0053249
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₈O₃
  • Molecular Weight 116.12
  • Synonym(s) 3-Furancarboxylic acid, tetrahydro-, (3S)-
  • SMILES OC(=O)[C@H]1CCOC1

Description

(S)-Tetrahydrofuran-3-carboxylic acid is a chiral building block featuring a stereodefined tetrahydrofuran ring fused to a carboxylic acid group. This configuration enables selective incorporation into bioactive molecules and synthetic intermediates where precise stereochemistry governs reactivity and biological activity. The molecule exhibits enhanced solubility in polar solvents and stability under standard bench conditions, facilitating use in peptide coupling, asymmetric synthesis, and medicinal chemistry applications.

Application

(S)-Tetrahydrofuran-3-carboxylic acid serves as a valuable chiral building block in medicinal chemistry, enabling the synthesis of bioactive heterocycles and peptide mimetics. Its well-defined stereochemistry and stability under standard reaction conditions facilitate efficient derivatization via amide coupling, esterification, and reduction. The molecule exhibits excellent functional group tolerance and is readily purified by recrystallization or chromatography, making it ideal for scalable synthesis of targeted scaffolds.

Synthesis

  • Route1
    • Benzyl (S)-tetrahydrofuran-3-carboxylate|CS-0495353
      130193-90-7
    • ~%
    • In-stock
      (S)-Tetrahydrofuran-3-carboxylic acid|CS-0053249
      168395-26-4

    References

    • US2013/165436 A1, ; Paragraph 0806; 0807; 0808 ;
  • Route2

    References

    • Song, Song; Zhu, Shou-Fei; Pu, Liu-Yang; Zhou, Qi-Lin Angewandte Chemie - International Edition, 2013 , vol. 52, # 23 p. 6072 - 6075 Angew. Chem., 2013 , vol. 125, # 23 p. 6188 - 6191
  • Route3

    References

    • US2013/165436 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 : H319
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   46.53
  • LogP   0.1075
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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