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    98541-64-1

    Catalog No. EBD43475

    CAS 98541-64-1

    Name N-(tert-Butoxycarbonyl)-L-serine beta-lactone

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    Basic Information

    Synonyms: N-(tert-Butoxycarbonyl)-L-serinebeta-lactone Butoxycarbonylserinebetalactone tert-butyl[(3S)-2-oxooxetan-3-yl]carbamate (s)-alpha-boc-amino-beta-propiolactone (s)-alpha-tert-butoxycarbonylamino-beta-propiolactone (s)-3-(tert-butoxycarbonylamino)-2-oxetanone n-boc-l-serinebeta-lactone [(3s)-2-oxo-3-oxetanyl]-1,1-dimethylethylestercarbamicacid n-bocl-serineb-lactone (s)-tert-butyl2-oxooxetan-3-ylcarbamate

    Molecular Formula: C8H13NO4

    Molecular Weight: 187.19

    Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Chiral Intermediates Synthetic Chemistry > Organic Building Blocks > Amines

    Product Description:
    N-(tert-Butoxycarbonyl)-L-serine beta-lactone is a chiral, protected serine-derived β-lactone. It is a white to off-white crystalline solid with a molecular formula of C8H13NO4. This compound is a versatile and crucial chiral building block in organic synthesis, particularly valued for its strained four-membered lactone ring, which is highly reactive towards nucleophilic ring-opening reactions. Its primary and most significant application is in the pharmaceutical industry as a key intermediate for the synthesis of various bioactive molecules. It is extensively used in the preparation of β-amino acids, peptide mimetics, and heterocyclic compounds. A prominent example is its role in the synthesis of protease inhibitors, such as HIV protease inhibitors (e.g., Atazanavir), where it introduces the critical (S)-3-amino-2-hydroxy-4-phenylbutanoyl (Ahp) pharmacophore or related structural motifs. The Boc-protected amino group and the reactive lactone allow for controlled, stereospecific incorporation of serine-derived fragments into complex molecular architectures. The compound should be stored under inert atmosphere at low temperatures (e.g., 2-8°C) to maintain stability. It is moisture-sensitive, and exposure to water can lead to hydrolysis of the lactone ring. Appropriate personal protective equipment should be used when handling this chemical.
    Physical Properties

    Boiling Point: 319 °C at 760 mmHg

    Flash Point: 146.7 °C

    Density: 1.18 g/cm3

    Storage: 2-8°C

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