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    22146-57-2

    Catalog No. EBD2216571

    CAS 22146-57-2

    Name (R)-2-Hydroxy-3,3-dimethylbutanoic acid

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    Basic Information

    Synonyms: (R)-2-Hydroxy-3,3-dimethylbutanoicacid (R)-(-)-3,3-Dimethyl-2-hydroxybutyricacid (R)-Trimethyllacticacid (2R)-2-hydroxy-3,3-dimethylbutanoicacid

    Molecular Formula: C6H12O3

    Molecular Weight: 132.16

    MDL Number: MFCD00211269

    Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Chiral Intermediates Synthetic Chemistry > Organic Building Blocks > Carboxylic Acids and Esters

    Product Description:
    (R)-2-Hydroxy-3,3-dimethylbutyric acid is a chiral α-hydroxy acid derivative characterized by a tertiary butyl group adjacent to the chiral center. This structural motif imparts significant steric hindrance, making it a valuable non-proteinogenic chiral building block in organic synthesis. Its primary and most significant application is in the pharmaceutical industry as a key chiral intermediate. It is notably used in the synthesis of complex active pharmaceutical ingredients (APIs). A prominent example is its role in the production of certain β-lactam antibiotics and other therapeutics where the introduction of a sterically demanding, chiral α-hydroxy acid moiety is crucial for biological activity and metabolic stability. Due to its defined stereochemistry and functional groups (carboxylic acid and hydroxyl), it serves as a versatile synthon in asymmetric synthesis and medicinal chemistry. It is employed in constructing peptide mimetics and other bioactive molecules, leveraging its ability to influence the pharmacokinetic and pharmacodynamic properties of the final drug candidate.
    Physical Properties

    Boiling Point: 242.4 °C at 760 mmHg

    Flash Point: 114.6 °C

    Density: 1.1 g/cm3

    mg g kg ml l t