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CS-W001157 4
Total: USD 88.00

Methyl 4-oxotetrahydrofuran-3-carboxylate

  • CAS No. 57595-23-0

  • Cat. No. CS-D0559
  • Purity≥96%
  • MDL No.MFCD19707049

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

Methyl 4-oxotetrahydrofuran-3-carboxylate|CS-D0559

Structure of 57595-23-0

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General Information

  • CAS No. 57595-23-0
  • Cat. No. CS-D0559
  • Purity ≥96%
  • MDL No. MFCD19707049
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₈O₄
  • Molecular Weight 144.13
  • Synonym(s) Tetrahydro-4-oxo-3-furancarboxylic Acid Methyl Ester
  • SMILES COC(C1COCC1=O)=O

Description

Methyl 4-oxotetrahydrofuran-3-carboxylate features a reactive α,β-unsaturated carbonyl system within a saturated heterocyclic framework, enabling efficient conjugate additions and cycloaddition reactions. This bench-stable ester integrates readily into complex molecular architectures, serving as a key intermediate in the synthesis of bioactive natural products and pharmaceutical candidates.

Application

Methyl 4-oxotetrahydrofuran-3-carboxylate serves as a versatile synthon in heterocyclic synthesis, enabling efficient access to tetrahydrofuran scaffolds via nucleophilic addition and cyclization reactions. Its α,β-unsaturated carbonyl motif facilitates Michael additions and condensations, while the ester group supports further functionalization. Bench-stable and readily purified by distillation or chromatography, it functions effectively in multistep sequences for medicinal chemistry and natural product synthesis.

Synthesis

  • Route1
    • In-stock
      Methyl 2-hydroxyacetate|CS-W004068
      96-35-5
    • null|null
      292638-85-8
    • ~26%
    • In-stock
      Methyl 4-oxotetrahydrofuran-3-carboxylate|CS-D0559
      57595-23-0

    References

    • Tran, Joe A.; Chen, Caroline W.; Tucci, Fabio C.; Jiang, Wanlong; Fleck, Beth A.; Chen, Chen Bioorganic and Medicinal Chemistry Letters, 2008 , vol. 18, # 3 p. 1124 - 1130
  • Route2
    • null|null
      292638-85-8
    • ~55%
    • In-stock
      Methyl 4-oxotetrahydrofuran-3-carboxylate|CS-D0559
      57595-23-0

    References

    • ELI LILLY AND COMPANY Patent: WO2004/94400 A2, 2004 ; Location in patent: Page 40 ; WO 2004/094400 A2
  • Route3
    • null|null
      798541-68-1
    • In-stock
      Methyl 2-hydroxyacetate|CS-W004068
      96-35-5
    • ~25%
    • In-stock
      Methyl 4-oxotetrahydrofuran-3-carboxylate|CS-D0559
      57595-23-0

    References

    • NEUROCRINE BIOSCIENCES, INC. Patent: WO2005/40109 A1, 2005 ; Location in patent: Page/Page column 78-79 ; WO 2005/040109 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

Quality Control

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Computational Chemistry Data

  • TPSA   52.6
  • LogP   -0.6251
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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