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CS-W001157 4
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(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2,3-dimethylbutanoic acid

  • CAS No. 169566-81-8

  • Cat. No. CS-W020179
  • Molecule weight353.42
  • Purity97%,94%ee
  • MDL No.MFCD08752490

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

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2,3-dimethylbutanoic acid|CS-W020179

Structure of 169566-81-8

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General Information

  • CAS No. 169566-81-8
  • Cat. No. CS-W020179
  • Purity 97%,94%ee
  • MDL No. MFCD08752490
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₁H₂₃NO₄
  • Molecular Weight 353.42
  • Synonym(s) None
  • SMILES CC(C)[C@](C)(NC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O)C(O)=O

Description

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2,3-dimethylbutanoic acid serves as a chiral, sterically hindered amino acid derivative for peptide synthesis. The fluorenylmethoxycarbonyl (Fmoc) group enables efficient N-terminal protection, while the branched aliphatic side chain enhances stability and solubility under standard coupling conditions.

Application

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2,3-dimethylbutanoic acid serves as a robust chiral building block for peptide synthesis, leveraging the stability and orthogonal deprotection of the Fmoc group. Its sterically hindered side chain enhances diastereoselectivity in coupling reactions, while the benzylic carbonyl facilitates mild removal under standard conditions. The molecule functions effectively in solid-phase and solution-phase workflows, offering reliable handling, clean purification, and compatibility with diverse synthetic transformations.

Synthesis

  • Route1
    • null|null
      4378-19-2
    • null|null
      28920-43-6
    • ~87%
    • In-stock
      (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2,3-dimethylbutanoic acid|CS-W020179
      169566-81-8

    References

    • Caporale; Gesiot; Sturlese; Wittelsberger; Mammi; Peggion Amino Acids, 2012 , vol. 43, # 1 p. 207 - 218
  • Route2
    • null|null
      616867-43-7
    • ~%
    • In-stock
      (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2,3-dimethylbutanoic acid|CS-W020179
      169566-81-8

    References

    • Spino, Claude; Gobdout, Cedrickx Journal of the American Chemical Society, 2003 , vol. 125, # 40 p. 12106 - 12107
  • Route3

    References

    • Spino, Claude; Gobdout, Cedrickx Journal of the American Chemical Society, 2003 , vol. 125, # 40 p. 12106 - 12107

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

Quality Control

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Computational Chemistry Data

  • TPSA   75.63
  • LogP   4.0244
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   5

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