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(S)-5-Oxo-tetrahydrofuran-2-carboxylic acid

  • CAS No. 21461-84-7

  • Cat. No. CS-D0218
  • Purity≥97%
  • MDL No.MFCD00064516

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

(S)-5-Oxo-tetrahydrofuran-2-carboxylic acid|CS-D0218

Structure of 21461-84-7

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General Information

  • CAS No. 21461-84-7
  • Cat. No. CS-D0218
  • Purity ≥97%
  • MDL No. MFCD00064516
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₆O₄
  • Molecular Weight 130.10
  • Synonym(s) (S)-(+)-γ-Carboxy-γ-butyrolactone
  • SMILES O=C([C@H](CC1)OC1=O)O

Description

(S)-5-Oxo-tetrahydrofuran-2-carboxylic acid features a chiral tetrahydrofuran core with a strategically positioned ketone and carboxylic acid, enabling selective transformations in asymmetric synthesis. This scaffold delivers high diastereoselectivity in cyclization reactions and serves as a key intermediate for bioactive heterocycles under standard bench conditions.

Synthesis

  • Route1

    References

    • Montagnat, Oliver D.; Lessene, Guillaume; Hughes, Andrew B. Journal of Organic Chemistry, 2010 , vol. 75, # 2 p. 390 - 398
  • Route2

    References

    • Salomon, Claudio J.; Mata, Ernesto G.; Mascaretti, Oreste A. Journal of Organic Chemistry, 1994 , vol. 59, # 24 p. 7259 - 7266
  • Route3

    References

    • Stone,K.J.; Little,R.D. Journal of the American Chemical Society, 1985 , vol. 107, p. 2495

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   63.6
  • LogP   -0.2234
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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