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rel-((1R,2S,4S)-7-(tert-Butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid)

  • CAS No. 500556-91-2

  • Cat. No. CS-0038879
  • Molecule weight241.28
  • Purity≥97%
  • MDL No.MFCD12198742

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

rel-((1R,2S,4S)-7-(tert-Butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid)|CS-0038879

Structure of 500556-91-2

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General Information

  • CAS No. 500556-91-2
  • Cat. No. CS-0038879
  • Purity ≥97%
  • MDL No. MFCD12198742
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₉NO₄
  • Molecular Weight 241.28
  • Synonym(s) (1S,2S,4R)-7-(tert-Butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid
  • SMILES CC(C)(OC(N1[C@H]2CC[C@@H]1[C@@H](C(O)=O)C2)=O)C

Description

This rel-((1R,2S,4S)-7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid) features a rigid, bicyclic scaffold with stereochemical control critical for conformationally constrained peptide mimetics. The tert-butoxycarbonyl group provides a stable, orthogonal protecting group for amine incorporation during synthetic sequences.

Application

rel-((1R,2S,4S)-7-(tert-Butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid serves as a stereochemically defined building block for the synthesis of bioactive nitrogen-containing heterocycles. The tert-butyl ester group enables convenient protection and orthogonal deprotection, while the bicyclic scaffold provides conformational rigidity ideal for medicinal chemistry campaigns. It functions effectively in amide coupling and hydrogenation reactions, offering reliable access to complex scaffolds with controlled stereochemistry.

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   1.859
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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