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    218943-30-7

    Catalog No. EBD10043

    CAS 218943-30-7

    Name (3S)-3-tert-butoxycarbonylamino-5-benzyloxycarbonylpentanoic acid

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    Basic Information

    Synonyms: (3S)-3-(tert-butoxycarbonylamino)hexanedioicacid6-benzylester (3S)-3-tert-butoxycarbonylamino-5-benzyloxycarbonylpentanoicacid Boc-L-beta-homoglutamicacid6-benzylester Boc-L-beta-homoglutamicacid(OBzl) (3S)-6-(benzyloxy)-3-[(tert-butoxycarbonyl)amino]-6-oxohexanoicacid

    Molecular Formula: C18H25NO6

    Molecular Weight: 351.39

    MDL Number: MFCD01862936

    Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Drug Synthesis Building Blocks Medicinal Chemistry > Biochemicals and Life Science Reagents > Peptides and Peptidomimetics

    Product Description:
    (3S)-3-tert-butoxycarbonylamino-5-benzyloxycarbonylpentanoic acid, also known as Boc-L-beta-homoglutamic acid 6-benzyl ester, is a protected derivative of the non-proteinogenic amino acid L-beta-homoglutamic acid. Its structure features two orthogonal protecting groups: a tert-butoxycarbonyl (Boc) group on the alpha-amino function and a benzyl (Bzl) ester on the side-chain carboxyl group. This configuration makes it a valuable chiral building block in solid-phase peptide synthesis (SPPS) and solution-phase peptide chemistry. This compound is primarily employed as a key intermediate in the synthesis of complex peptides and peptidomimetics. The Boc protecting group is acid-labile, allowing for selective deprotection under conditions that leave the benzyl ester intact, which is typically removed by hydrogenolysis. Its main application lies in introducing the beta-homoglutamic acid residue into peptide sequences. Beta-homoglutamic acid, an analog of glutamic acid with an extended side chain, is used in medicinal chemistry to modulate peptide conformation, stability, and interactions with biological targets, particularly in the development of enzyme inhibitors or receptor ligands. As a specialized, protected amino acid derivative, it is not considered a generic synthetic reagent. Its use is almost exclusively confined to advanced peptide research and the synthesis of potential therapeutic agents, underscoring its role in pharmaceutical development rather than general organic synthesis.
    Physical Properties

    Boiling Point: 530 °C at 760 mmHg

    Flash Point: 274.4 °C

    Density: 1.178 g/cm3

    mg g kg ml l t