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(S)-tert-Butyl 5-bromo-2-((tert-butoxycarbonyl)amino)pentanoate

  • CAS No. 91229-86-6

  • Cat. No. CS-0154599
  • Molecule weight352.26
  • Purity≥95%
  • MDL No.MFCD22576481

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

(S)-tert-Butyl 5-bromo-2-((tert-butoxycarbonyl)amino)pentanoate|CS-0154599

Structure of 91229-86-6

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General Information

  • CAS No. 91229-86-6
  • Cat. No. CS-0154599
  • Purity ≥95%
  • MDL No. MFCD22576481
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₂₆BrNO₄
  • Molecular Weight 352.26
  • Synonym(s) N-Boc-5-bromo-L-norvaline tert-butyl ester
  • SMILES CC(C)(OC([C@@H](NC(OC(C)(C)C)=O)CCCBr)=O)C

Description

(S)-tert-Butyl 5-bromo-2-((tert-butoxycarbonyl)amino)pentanoate is a stereochemically defined, bench-stable building block for peptide and peptidomimetic synthesis. The molecule integrates a bromoalkyl side chain with a protected amino group, enabling site-specific conjugation and downstream functionalization under standard conditions.

Application

(S)-tert-Butyl 5-bromo-2-((tert-butoxycarbonyl)amino)pentanoate serves as a versatile chiral building block for the synthesis of amino acid derivatives and peptidomimetics. The pendant bromide enables facile late-stage functionalization via palladium-catalyzed cross-coupling, while the Boc-protected amine ensures compatibility with diverse reaction conditions. Bench-stable and readily purified by flash chromatography, it facilitates efficient access to complex scaffolds in medicinal chemistry campaigns.

Synthesis

  • Route1
    • 5-Benzyl 1-(tert-butyl) L-glutamate|CS-0488171
      80165-23-7
    • ~%
    • In-stock
      (S)-tert-Butyl 5-bromo-2-((tert-butoxycarbonyl)amino)pentanoate|CS-0154599
      91229-86-6

    References

    • Olsen; Ramasamy; Emery Journal of Organic Chemistry, 1984 , vol. 49, # 19 p. 3527 - 3534
  • Route2

    References

    • Olsen; Ramasamy; Emery Journal of Organic Chemistry, 1984 , vol. 49, # 19 p. 3527 - 3534
  • Route3
    • null|null
      28812-54-6
    • ~%
    • In-stock
      (S)-tert-Butyl 5-bromo-2-((tert-butoxycarbonyl)amino)pentanoate|CS-0154599
      91229-86-6

    References

    • Olsen; Ramasamy; Emery Journal of Organic Chemistry, 1984 , vol. 49, # 19 p. 3527 - 3534

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

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Computational Chemistry Data

  • TPSA   64.63
  • LogP   3.3965
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   5

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