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N-9-Fluorenylmethoxycarbonylaspartic acid β-methyl ester

  • CAS No. 145038-53-5

  • Cat. No. CS-0019420
  • Purity≥98%
  • MDL No.MFCD08458573

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

N-9-Fluorenylmethoxycarbonylaspartic acid β-methyl ester|CS-0019420

Structure of 145038-53-5

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General Information

  • CAS No. 145038-53-5
  • Cat. No. CS-0019420
  • Purity ≥98%
  • MDL No. MFCD08458573
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₀H₁₉NO₆
  • Molecular Weight 369.37
  • Synonym(s) None
  • SMILES O=C(OC)C[C@@H](C(O)=O)NC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O

Description

N-9-Fluorenylmethoxycarbonylaspartic acid β-methyl ester features a fluorenylmethoxycarbonyl (Fmoc) group for orthogonal protection in peptide synthesis, paired with a β-methyl ester that enhances metabolic stability. This derivative enables efficient incorporation of aspartic acid analogs into complex sequences under standard coupling conditions, offering improved solubility and reduced side reactions during chain elongation.

Application

N-9-Fluorenylmethoxycarbonylaspartic acid β-methyl ester serves as a robust diacid building block for peptide synthesis, enabling selective protection of both α- and β-carboxyl groups. Its fluorenylmethoxycarbonyl (Fmoc) group ensures orthogonal deprotection under mild basic conditions, while the β-methyl ester enhances metabolic stability and modulates steric profile. The compound exhibits excellent bench stability, simplifies purification, and functions reliably in standard solid-phase and solution-phase workflows.

Synthesis

  • Route1

    References

    • Jamieson, Andrew G.; Boutard, Nicolas; Beauregard, Kim; Bodas, Mandar S.; Ong, Huy; et al. Journal of the American Chemical Society, 2009 , vol. 131, p. 7917 - 7927
  • Route2

    References

    • WO2010/105367 A1, ; Page/Page column 35; 36; 37 ;
  • Route3

    References

    • Journal of Organic Chemistry, , vol. 72, # 17 p. 6599 - 6601

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   101.93
  • LogP   2.5414
  • H_Acceptors   5
  • H_Donors   2
  • Rotatable_Bonds   6

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