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    26787-75-7

    Catalog No. EBD311366

    CAS 26787-75-7

    Name (R)-(N-benzyloxycarbonyl)-p-hydroxyphenylglycine

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    Basic Information

    Synonyms: (R)-(N-benzyloxycarbonyl)-p-hydroxyphenylglycine N-(benzyloxycarbonyl)-D-(p-hydroxyphenyl)glycine (R)-N-benzyloxycarbonyl-4-hydroxyphenylglycine

    Molecular Formula: C16H15NO5

    Molecular Weight: 301.3

    Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Chiral Intermediates Medicinal Chemistry > Biochemicals and Life Science Reagents > Amino Acids and Derivatives

    Product Description:
    (R)-(N-benzyloxycarbonyl)-p-hydroxyphenylglycine is a chiral, non-proteinogenic amino acid derivative. Its structure features a D-configuration (R-enantiomer) at the alpha carbon, a p-hydroxyphenyl side chain, and an N-terminal benzyloxycarbonyl (Cbz) protecting group. This combination makes it a valuable, optically pure building block. This compound is primarily employed as a key chiral intermediate in the synthesis of pharmaceuticals, particularly β-lactam antibiotics. Its most notable application is in the industrial production of semi-synthetic penicillins and cephalosporins, such as amoxicillin. The chiral integrity of the D-2-(4-hydroxyphenyl)glycine moiety is crucial for the biological activity of these antibiotics. The Cbz group serves to protect the amine functionality during synthetic steps, allowing for selective reactions. As a specialty fine chemical, it is produced on a commercial scale to meet the demands of the antibiotic manufacturing industry. Its synthesis and supply are critical for ensuring the availability of broad-spectrum antibacterial agents.
    Physical Properties
    mg g kg ml l t