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CS-W001157 4
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endo-3-[(tert-Butoxy)carbonyl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid

  • CAS No. 1401464-07-0

  • Cat. No. CS-0036377
  • Purity≥98%
  • MDL No.MFCD12198805

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

endo-3-[(tert-Butoxy)carbonyl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid|CS-0036377

Structure of 1401464-07-0

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General Information

  • CAS No. 1401464-07-0
  • Cat. No. CS-0036377
  • Purity ≥98%
  • MDL No. MFCD12198805
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₇NO₄
  • Molecular Weight 227.26
  • Synonym(s) (Meso-1R,5S,6S)-3-(Tert-Butoxycarbonyl)-3-Azabicyclo[3.1.0]Hexane-6-Carboxylic Acid
  • SMILES OC([C@@H]1[C@@]2([H])[C@]1([H])CN(C2)C(OC(C)(C)C)=O)=O

Description

This azabicyclic scaffold integrates a protected amine and carboxylic acid within a rigid, electron-deficient framework. Designed for efficient peptide macrocyclization, it enables stable ring formation under standard conditions. The tert-butoxycarbonyl group offers orthogonal protection, while the endo configuration enhances conformational control in synthetic applications.

Application

endo-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, hydrogenation, and cyclization protocols. Its rigid bicyclic framework supports stereocontrolled derivatization, making it well-suited for targeted compound library development.

Safety Information

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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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