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(1R,2S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclohexane-1-carboxylic acid

  • CAS No. 312965-06-3

  • Cat. No. CS-0166879
  • Purity≥95%
  • MDL No.MFCD06410974

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

(1R,2S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclohexane-1-carboxylic acid|CS-0166879

Structure of 312965-06-3

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General Information

  • CAS No. 312965-06-3
  • Cat. No. CS-0166879
  • Purity ≥95%
  • MDL No. MFCD06410974
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₂H₂₃NO₄
  • Molecular Weight 365.42
  • Synonym(s) (1R,2S)-Fmoc-Achc
  • SMILES O=C([C@H]1[C@@H](NC(OCC2C3=C(C4=C2C=CC=C4)C=CC=C3)=O)CCCC1)O

Description

This fluorenylmethoxycarbonyl-protected cyclohexyl amino acid derivative features a rigid, chiral scaffold ideal for peptide synthesis. The Fmoc group enables efficient orthogonal protection, while the cyclohexane ring imparts conformational stability. Designed for seamless incorporation into solid-phase workflows, it offers high solubility and predictable coupling efficiency under standard conditions.

Application

(1R,2S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclohexane-1-carboxylic acid serves as a chiral building block for peptide synthesis, leveraging the robustness of Fmoc protection. Its cyclohexyl backbone provides conformational rigidity, enhancing stereochemical control in target-directed synthesis. The Fmoc group enables orthogonal deprotection under mild basic conditions, facilitating efficient coupling and purification workflows. This compound exhibits excellent bench stability and compatibility with standard solid-phase and solution-phase protocols.

Synthesis

  • Route1
    • (1R,6S)-7-Azabicyclo[4.2.0]octan-8-one|CS-1058327
      874292-57-6
    • ~%
    • In-stock
      (1R,2S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclohexane-1-carboxylic acid|CS-0166879
      312965-06-3

    References

    • Journal of the American Chemical Society, , vol. 133, # 12 p. 4246 - 4249
  • Route2

    References

    • Journal of the American Chemical Society, , vol. 133, # 12 p. 4246 - 4249
  • Route3
    • null|null
      285560-90-9
    • ~%
    • In-stock
      (1R,2S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclohexane-1-carboxylic acid|CS-0166879
      312965-06-3

    References

    • Journal of the American Chemical Society, , vol. 133, # 12 p. 4246 - 4249

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   75.63
  • LogP   4.1685
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   4

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