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CS-W001157 4
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(R)-4-((Tert-butoxycarbonyl)amino)-5-methoxy-5-oxopentanoic acid

  • CAS No. 55227-00-4

  • Cat. No. CS-0169313
  • Purity≥95%
  • MDL No.MFCD00076930

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

(R)-4-((Tert-butoxycarbonyl)amino)-5-methoxy-5-oxopentanoic acid|CS-0169313

Structure of 55227-00-4

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General Information

  • CAS No. 55227-00-4
  • Cat. No. CS-0169313
  • Purity ≥95%
  • MDL No. MFCD00076930
  • Storage 4°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₉NO₆
  • Molecular Weight 261.27
  • Synonym(s) Boc-D-glu-ome
  • SMILES O=C(O)CC[C@H](C(OC)=O)NC(OC(C)(C)C)=O

Description

(R)-4-((Tert-butoxycarbonyl)amino)-5-methoxy-5-oxopentanoic acid is a chiral building block featuring a protected amine and orthogonal functional groups. This stable, bench-ready intermediate integrates seamlessly into peptide synthesis and bioconjugation workflows, enabling efficient access to complex molecular architectures through selective derivatization.

Application

(R)-4-((Tert-butoxycarbonyl)amino)-5-methoxy-5-oxopentanoic acid serves as a versatile chiral building block for the synthesis of bioactive heterocycles and peptide-derived scaffolds. Its orthogonal functionality—tert-butoxycarbonyl (Boc) amine, ester, and ketone groups—enables sequential transformations under standard conditions. The molecule exhibits excellent bench stability, facilitates straightforward purification, and participates reliably in nucleophilic additions, cyclizations, and reductive aminations, making it valuable for medicinal chemistry campaigns requiring stereocontrolled access to complex frameworks.

Synthesis

  • Route1
    • 5-Benzyl 1-methyl (tert-butoxycarbonyl)-d-glutamate|CS-0686466
      110473-10-4
    • ~99%
    • In-stock
      (R)-4-((Tert-butoxycarbonyl)amino)-5-methoxy-5-oxopentanoic acid|CS-0169313
      55227-00-4

    References

    • Hu, Tao; Panek, James S. Journal of the American Chemical Society, 2002 , vol. 124, # 38 p. 11368 - 11378
  • Route2

    References

    • Cluzeau, Jerome; Oishi, Shinya; Ohno, Hiroaki; Wang, Zixuan; Evans, Barry; Peiper, Stephen C.; Fujii, Nobutaka Organic and Biomolecular Chemistry, 2007 , vol. 5, # 12 p. 1915 - 1923
  • Route3

    References

    • Cluzeau, Jerome; Oishi, Shinya; Ohno, Hiroaki; Wang, Zixuan; Evans, Barry; Peiper, Stephen C.; Fujii, Nobutaka Organic and Biomolecular Chemistry, 2007 , vol. 5, # 12 p. 1915 - 1923

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   101.93
  • LogP   0.9175
  • H_Acceptors   5
  • H_Donors   2
  • Rotatable_Bonds   5

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