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(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-7-(tert-butoxy)-7-oxoheptanoic acid

  • CAS No. 159751-46-9

  • Cat. No. CS-0101030
  • Purity≥96%
  • MDL No.MFCD08166552

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

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-7-(tert-butoxy)-7-oxoheptanoic acid|CS-0101030

Structure of 159751-46-9

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General Information

  • CAS No. 159751-46-9
  • Cat. No. CS-0101030
  • Purity ≥96%
  • MDL No. MFCD08166552
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₆H₃₁NO₆
  • Molecular Weight 453.53
  • Synonym(s) (S)-2-FMOC-AMINO-HEPTANEDIOIC ACID 7-TERT-BUTYL ESTER
  • SMILES O=C(O)[C@@H](NC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O)CCCCC(OC(C)(C)C)=O

Description

This fluorenylmethoxycarbonyl-protected amino acid derivative features a sterically hindered tert-butoxy group and a reactive ketone moiety, enabling selective conjugation in peptide synthesis. The C-terminal carboxylic acid facilitates efficient coupling under standard conditions, while the bench-stable fluorenylmethyl carbamate safeguards the amine during iterative assembly.

Application

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-7-(tert-butoxy)-7-oxoheptanoic acid serves as a robust chiral building block for peptide synthesis, enabling efficient N-terminal protection and side-chain functionalization. The fluorenylmethoxycarbonyl (Fmoc) group ensures high stability and orthogonal deprotection under mild basic conditions. The tert-butoxy carbonyl moiety provides a readily cleavable auxiliary for selective transformations, while the β-ketoacid functionality facilitates downstream cyclizations and heterocycle formation. Its bench-stable solid form simplifies handling and purification in multi-step syntheses.

Synthesis

  • Route1
    • null|null
      868754-94-3
    • ~94%
    • In-stock
      (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-7-(tert-butoxy)-7-oxoheptanoic acid|CS-0101030
      159751-46-9

    References

    • Ryan, Shannon J.; Zhang, Yongda; Kennan, Alan J. Organic Letters, 2005 , vol. 7, # 21 p. 4765 - 4767
  • Route2

    References

    • Ryan, Shannon J.; Zhang, Yongda; Kennan, Alan J. Organic Letters, 2005 , vol. 7, # 21 p. 4765 - 4767
  • Route3

    References

    • Ryan, Shannon J.; Zhang, Yongda; Kennan, Alan J. Organic Letters, 2005 , vol. 7, # 21 p. 4765 - 4767

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-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   101.93
  • LogP   4.8804
  • H_Acceptors   5
  • H_Donors   2
  • Rotatable_Bonds   9

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