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(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-((tert-butoxycarbonyl)amino)-2-methylhexanoic acid

  • CAS No. 1202003-49-3

  • Cat. No. CS-0101052
  • Purity≥97%
  • MDL No.MFCD17019258

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

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-((tert-butoxycarbonyl)amino)-2-methylhexanoic acid|CS-0101052

Structure of 1202003-49-3

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General Information

  • CAS No. 1202003-49-3
  • Cat. No. CS-0101052
  • Purity ≥97%
  • MDL No. MFCD17019258
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₇H₃₄N₂O₆
  • Molecular Weight 482.57
  • Synonym(s) N6-[(1,1-Dimethylethoxy)carbonyl]-N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-2-methyl-L-lysine
  • SMILES O=C(O)[C@@](CCCCNC(OC(C)(C)C)=O)(C)NC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O

Description

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-((tert-butoxycarbonyl)amino)-2-methylhexanoic acid features a sterically hindered aliphatic chain flanked by orthogonal protecting groups: the Fmoc moiety at the α-amino position and a Boc group at the ε-amino site. This configuration enables selective deprotection during peptide synthesis, facilitating efficient incorporation of hydrophobic, branched amino acid residues into complex sequences under standard conditions.

Application

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-((tert-butoxycarbonyl)amino)-2-methylhexanoic acid serves as a versatile chiral building block for peptide synthesis, enabling efficient N-terminal protection and side-chain functionalization. The Fmoc group facilitates orthogonal deprotection under mild basic conditions, while the Boc-protected lysine-like side chain allows for selective modification. Its bench-stable nature and compatibility with standard coupling reagents make it ideal for solid-phase and solution-phase peptide assembly workflows.

Synthesis

  • Route1
    • In-stock
      Di-tert-butyl dicarbonate|CS-0017817
      24424-99-5
    • null|null
      1453178-51-2
    • ~94%
    • In-stock
      (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-((tert-butoxycarbonyl)amino)-2-methylhexanoic acid|CS-0101052
      1202003-49-3

    References

    • Banerjee, Souvik; Wiggins, Walker J.; Geoghegan, Jessie L.; Anthony, Catherine T.; Woltering, Eugene A.; Masterson, Douglas S. Organic and Biomolecular Chemistry, 2013 , vol. 11, # 37 p. 6307 - 6319
  • Route2

    References

    • Chauhan, Satendra S. Tetrahedron Letters, 2009 , vol. 50, # 49 p. 6913 - 6915
  • Route3
    • null|null
      17377-68-3
    • ~%
    • In-stock
      (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-((tert-butoxycarbonyl)amino)-2-methylhexanoic acid|CS-0101052
      1202003-49-3

    References

    • Banerjee, Souvik; Wiggins, Walker J.; Geoghegan, Jessie L.; Anthony, Catherine T.; Woltering, Eugene A.; Masterson, Douglas S. Organic and Biomolecular Chemistry, 2013 , vol. 11, # 37 p. 6307 - 6319

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   113.96
  • LogP   5.0634
  • H_Acceptors   5
  • H_Donors   3
  • Rotatable_Bonds   9

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