Welcome to iChemical.com!

In the below part, please select the country you want us to ship to: Please note that once you've selected a shipping country, all pricing information on our website will be automatically updated to include door-to-door shipping to the country you specified.

    OK
    Get Quote Login
    273222-06-3

    Catalog No. EBD4059473

    CAS 273222-06-3

    Name (2S,4R)-4-{[(tert-butoxy)carbonyl]amino}-1-{[(9H-fluoren-9-yl)methoxy]carbonyl}pyrrolidine-2-carboxylic acid

    Get Quote
    Basic Information

    Molecular Formula: C25H28N2O6

    Molecular Weight: 452.507

    Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Heterocyclic Intermediates Medicinal Chemistry > Biochemicals and Life Science Reagents > Peptides and Peptidomimetics

    Product Description:
    This compound, (2S,4R)-4-{[(tert-butoxy)carbonyl]amino}-1-{[(9H-fluoren-9-yl)methoxy]carbonyl}pyrrolidine-2-carboxylic acid, is a protected amino acid derivative featuring a pyrrolidine ring. It is a key chiral building block in solid-phase peptide synthesis (SPPS). The molecule incorporates two orthogonal protecting groups: the 9-fluorenylmethoxycarbonyl (Fmoc) group on the amine nitrogen and the tert-butoxycarbonyl (Boc) group on the side-chain amine. The Fmoc group is base-labile and is standardly used for temporary α-amino protection in Fmoc-SPPS, while the Boc group is acid-labile, providing orthogonal protection for the side chain functionality. Its primary and well-defined application is as a specialized, non-proteinogenic amino acid precursor for the synthesis of peptides and peptidomimetics. The (2S,4R) stereochemistry of the proline-like structure is crucial for introducing conformational constraints into peptide chains, which can enhance metabolic stability, receptor selectivity, and biological activity. It is extensively used in medicinal chemistry research for developing therapeutic peptides, protease inhibitors, and other bioactive molecules targeting various diseases. This compound is a high-value synthetic intermediate rather than a final API. It is commercially available from suppliers specializing in peptide synthesis reagents and advanced pharmaceutical intermediates. Handling requires standard precautions for laboratory chemicals, and it should be stored under inert conditions to preserve its stability.
    Physical Properties
    mg g kg ml l t