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CS-W001157 4
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(R)-4-(((Benzyloxy)carbonyl)amino)-5-methoxy-5-oxopentanoic acid

  • CAS No. 26566-11-0

  • Cat. No. CS-0129470
  • Purity≥98%
  • MDL No.MFCD00798654

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

(R)-4-(((Benzyloxy)carbonyl)amino)-5-methoxy-5-oxopentanoic acid|CS-0129470

Structure of 26566-11-0

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General Information

  • CAS No. 26566-11-0
  • Cat. No. CS-0129470
  • Purity ≥98%
  • MDL No. MFCD00798654
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₇NO₆
  • Molecular Weight 295.29
  • Synonym(s) z-d-Glu-ome
  • SMILES O=C(O)CC[C@@H](NC(OCC1=CC=CC=C1)=O)C(OC)=O

Description

(R)-4-(((Benzyloxy)carbonyl)amino)-5-methoxy-5-oxopentanoic acid features a chiral center at the C4 position, enabling stereocontrolled synthesis in peptide and macrocycle workflows. The benzyloxycarbonyl (Cbz) group provides robust N-terminal protection, while the methoxy-ketone functionality offers a handle for selective derivatization under mild conditions. This compound combines stability with orthogonal reactivity, streamlining access to complex scaffolds.

Application

(R)-4-(((Benzyloxy)carbonyl)amino)-5-methoxy-5-oxopentanoic acid serves as a versatile building block for the synthesis of β-amino carbonyl compounds and heterocyclic scaffolds. Its well-defined stereochemistry and orthogonal functionality—combining a benzyl ester, amine, and α-ketoester group—enable selective transformations in peptide-like sequences and complex molecule assembly. Bench-stable and amenable to standard purification methods, it facilitates efficient downstream derivatization in medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • Van Heerbeek, Rieko; Kamer, Paul C. J.; Van Leeuwen, Piet N.M.W.; Reek, Joost N.H. Organic and Biomolecular Chemistry, 2006 , vol. 4, # 2 p. 211 - 223
  • Route2
    • null|null
      67-56-1
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      97975-57-0
    • ~91%
    • In-stock
      (R)-4-(((Benzyloxy)carbonyl)amino)-5-methoxy-5-oxopentanoic acid|CS-0129470
      26566-11-0

    References

    • Shirude, Pravin S.; Kumar, Vaijayanti A.; Ganesh, Krishna N. Tetrahedron, 2004 , vol. 60, # 42 p. 9485 - 9491
  • Route3

    References

    • Van Heerbeek, Rieko; Kamer, Paul C. J.; Van Leeuwen, Piet N.M.W.; Reek, Joost N.H. Organic and Biomolecular Chemistry, 2006 , vol. 4, # 2 p. 211 - 223

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

Quality Control

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Computational Chemistry Data

  • TPSA   101.93
  • LogP   1.3192
  • H_Acceptors   5
  • H_Donors   2
  • Rotatable_Bonds   7

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