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CS-W001157 4
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5-(Benzyloxycarbonyl)pentanoic acid

  • CAS No. 40542-90-3

  • Cat. No. CS-0131742
  • Purity≥95%
  • MDL No.MFCD00441728

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

5-(Benzyloxycarbonyl)pentanoic acid|CS-0131742

Structure of 40542-90-3

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General Information

  • CAS No. 40542-90-3
  • Cat. No. CS-0131742
  • Purity ≥95%
  • MDL No. MFCD00441728
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₆O₄
  • Molecular Weight 236.26
  • Synonym(s) Adipic acid monobenzyl ester
  • SMILES O=C(O)CCCCC(OCC1=CC=CC=C1)=O

Description

5-(Benzyloxycarbonyl)pentanoic acid features a benzyl-protected carboxylic acid handle ideal for peptide synthesis and conjugation chemistry. This bench-stable, moisture-tolerant reagent integrates seamlessly into functionalization workflows, offering reliable coupling efficiency under standard conditions.

Application

5-(Benzyloxycarbonyl)pentanoic acid serves as a versatile bifunctional building block for peptide and macrocyclic synthesis, enabling efficient incorporation of C-terminal carboxylic acid and Nα-protected amine handles. The benzyloxycarbonyl (Z) group provides robust protection under standard conditions with orthogonal cleavage via hydrogenolysis, while the aliphatic chain offers flexibility for ring formation. Bench-stable and compatible with common coupling reagents, it facilitates clean functionalization in solid-phase and solution-phase workflows.

Synthesis

  • Route1

    References

    • Colson, Yolonda; Azouz, Solomon; Grinstaff, Mark; Wolinsky, Jesse; Griset, Aaron Patent: US2008/75718 A1, 2008 ; Location in patent: Page/Page column 41 ;
  • Route2

    References

    • Kar, Nilanjana; Liu, Haoyu; Edgar, Kevin J. Biomacromolecules, 2011 , vol. 12, # 4 p. 1106 - 1115
  • Route3
    • null|null
      78277-26-6
    • ~87%
    • In-stock
      5-(Benzyloxycarbonyl)pentanoic acid|CS-0131742
      40542-90-3

    References

    • Matt, Christophe; Wagner, Alain; Mioskowski, Charles Journal of Organic Chemistry, 1997 , vol. 62, # 2 p. 234 - 235

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   63.6
  • LogP   2.3748
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   7

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