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CS-W001157 4
Total: USD 88.00

exo-3-[(tert-Butoxy)carbonyl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid

  • CAS No. 927679-54-7

  • Cat. No. CS-0035497
  • Purity≥97%
  • MDL No.None

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

exo-3-[(tert-Butoxy)carbonyl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid|CS-0035497

Structure of 927679-54-7

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General Information

  • CAS No. 927679-54-7
  • Cat. No. CS-0035497
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₇NO₄
  • Molecular Weight 227.26
  • Synonym(s) exo-3-Boc-3-azabicyclo[3.1.0]hexane-6-carboxylic acid
  • SMILES CC(C)(C)OC(=O)N1C[C@H]2[C@@H](C1)[C@@H]2C(=O)O

Description

exo-3-[(tert-Butoxy)carbonyl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid features a rigid, electron-deficient bicyclic scaffold that enables precise stereocontrol in asymmetric synthesis. The tert-butoxycarbonyl group provides stable protection under standard conditions, while the carboxylic acid functionality offers direct handle for peptide coupling and derivatization. This bench-stable building block integrates readily into complex molecular architectures requiring defined spatial orientation.

Application

exo-3-[(tert-Butoxy)carbonyl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid serves as a versatile, bench-stable building block for the synthesis of constrained nitrogen-containing heterocycles. The protected amine and carboxylic acid functionalities enable orthogonal transformations, facilitating efficient access to medicinal chemistry scaffolds via standard coupling, reduction, and cyclization protocols. Its rigid bicyclic core enhances conformational control in target molecule design.

Synthesis

  • Route1

    References

    • Org. Process Res. Dev., , vol. 15, # 5 p. 1052 - 1062
  • Route2
    • (1R,5S,6r)-3-tert-Butyl 6-ethyl 3-azabicyclo[3.1.0]hexane-3,6-dicarboxylate|CS-0499176
      134575-37-4
    • ~%
    • In-stock
      exo-3-[(tert-Butoxy)carbonyl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid|CS-0035497
      927679-54-7

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 24, # 4 p. 1067 - 1070
  • Route3
    • (1R,5S,6r)-2,4-dioxo-3-oxabicyclo[3.1.0]Hexane-6-carboxylic acid|CS-0521198
      187681-87-4
    • ~%
    • In-stock
      exo-3-[(tert-Butoxy)carbonyl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid|CS-0035497
      927679-54-7

    References

    • Org. Process Res. Dev., , vol. 15, # 5 p. 1052 - 1062

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   66.84
  • LogP   1.1839
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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