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cis-3-Oxabicyclo[3.1.0]hexane-6-carboxylic acid

  • CAS No. 55685-58-0

  • Cat. No. CS-0049697
  • Molecule weight128.13
  • Purity≥97%
  • MDL No.MFCD19230128

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

cis-3-Oxabicyclo[3.1.0]hexane-6-carboxylic acid|CS-0049697

Structure of 55685-58-0

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General Information

  • CAS No. 55685-58-0
  • Cat. No. CS-0049697
  • Purity ≥97%
  • MDL No. MFCD19230128
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₈O₃
  • Molecular Weight 128.13
  • Synonym(s) None
  • SMILES [H][C@@]12COC[C@@]1([C@@H]2C(O)=O)[H]

Description

cis-3-Oxabicyclo[3.1.0]hexane-6-carboxylic acid features a rigid, strained bicyclic scaffold with a strategically positioned carboxylic acid group. The fused oxygen atom imparts polarity and enhances solubility, while the cis-configured ring system ensures defined stereochemical control. This structural motif enables precise molecular presentation in synthetic applications requiring constrained geometry and tailored reactivity.

Application

cis-3-Oxabicyclo[3.1.0]hexane-6-carboxylic acid serves as a rigid, bicyclic scaffold for medicinal chemistry and synthetic organic applications. Its constrained geometry enables precise spatial orientation of functional groups, facilitating stereocontrolled synthesis. The carboxylic acid moiety offers direct handle for derivatization, while the oxabridge enhances metabolic stability and modulates physicochemical properties. Bench-stable and compatible with standard coupling protocols, it functions effectively in peptide conjugation and heterocycle construction workflows.

Safety Information

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Computational Chemistry Data

  • TPSA   46.53
  • LogP   -0.0366
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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