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CS-W001157 4
Total: USD 88.00

L-Pyroglutamic acid ethyl ester

  • CAS No. 7149-65-7

  • Cat. No. CS-W020688
  • Purity≥97%
  • MDL No.MFCD00064497

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

L-Pyroglutamic acid ethyl ester|CS-W020688

Structure of 7149-65-7

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General Information

  • CAS No. 7149-65-7
  • Cat. No. CS-W020688
  • Purity ≥97%
  • MDL No. MFCD00064497
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₁₁NO₃
  • Molecular Weight 157.17
  • Synonym(s) None
  • SMILES O=C1CC[C@@H](C(OCC)=O)N1

Description

L-Pyroglutamic acid ethyl ester features a stable cyclic imide structure with a pendant ethyl ester group, enabling straightforward hydrolysis to the parent acid. This derivative enhances solubility and stability in organic solvents, facilitating its use in peptide synthesis and chemical biology applications.

Application

L-Pyroglutamic acid ethyl ester serves as a versatile chiral building block for peptide and heterocyclic synthesis, offering bench-stable functionality with predictable reactivity in amide bond formation and cyclization protocols. Its protected γ-lactam core enables straightforward access to pyrrolidine-based scaffolds common in medicinal chemistry, with high compatibility in standard coupling reactions and ease of purification via flash chromatography.

Synthesis

  • Route1
    • null|null
      64-17-5
    • In-stock
      L-Pyroglutamic acid|CS-M0659
      98-79-3
    • ~96%
    • In-stock
      L-Pyroglutamic acid ethyl ester|CS-W020688
      7149-65-7

    References

    • FORSCHUNGSVERBUND BERLIN E.V. Patent: US2011/34438 A1, 2011 ; Location in patent: Page/Page column 20 ;
  • Route2

    References

    • WO2012/48421 A1, ; Page/Page column 26-27 ;
  • Route3
    • null|null
      64-17-5
    • In-stock
      L-Glutamic acid|CS-0003473
      56-86-0
    • ~95%
    • In-stock
      L-Pyroglutamic acid ethyl ester|CS-W020688
      7149-65-7

    References

    • Miyata, Okiko; Shirai, Atsushi; Yoshino, Shintaro; Takeda, Yoshifumi; Sugiura, Makiko; Naito, Takeaki Synlett, 2006 , # 6 p. 893 - 896

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

Quality Control

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Computational Chemistry Data

  • TPSA   55.4
  • LogP   -0.1719
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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