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    16159-70-9

    Catalog No. EBD273487

    CAS 16159-70-9

    Name (R)-4-Nitrophenyl 2-((tert-butoxycarbonyl)amino)-3-phenylpropanoate

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    Basic Information

    Synonyms: boc-D-phenylalanine4-nitrophenylester Boc-D-Phe-ONp 4-nitrophenylN-(tert-butoxycarbonyl)-D-phenylalaninate (R)-4-Nitrophenyl2-((tert-butoxycarbonyl)amino)-3-phenylpropanoate

    Molecular Formula: C20H22N2O6

    Molecular Weight: 386.4

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

    Product Description:
    (R)-4-Nitrophenyl 2-((tert-butoxycarbonyl)amino)-3-phenylpropanoate is a protected amino acid active ester derivative. It features a Boc-protected D-phenylalanine core coupled to a 4-nitrophenol leaving group. This compound is a white to off-white crystalline powder with a molecular formula of C20H22N2O6. This product is primarily used as a key building block in peptide synthesis, particularly for solid-phase peptide synthesis (SPPS) and solution-phase methods. The active ester (4-nitrophenyl ester) is highly reactive towards nucleophiles like amines, facilitating efficient amide bond formation to incorporate D-phenylalanine into peptide sequences. The tert-butoxycarbonyl (Boc) group serves as a standard amine protecting group that is stable under basic conditions and can be cleanly removed under acidic conditions, making it a crucial reagent for constructing peptides with specific stereochemistry and sequence. As a derivative of a non-natural D-amino acid, it is valuable for creating peptides with enhanced metabolic stability, altered biological activity, or specific structural properties for research in medicinal chemistry and biochemistry. It is a specialized reagent rather than a general-purpose synthesis block.
    Physical Properties
    mg g kg ml l t