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    198828-94-3

    Catalog No. EBD2208434

    CAS 198828-94-3

    Name (L)-(1S,2S)-N-(benzyloxycarbonyl)-O-tert-butylthreonine dicyclohexylamine salt

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    Basic Information

    Synonyms: (L)-(1S,2S)-N-(benzyloxycarbonyl)-O-tert-butylthreoninedicyclohexylaminesalt n-alpha-carbobenzoxy-o-t-butyl-l-allo-threoninedicyclohexylammoniumsalt z-allo-thr(tbu)-ohdcha z-allo-threonine(tbu)-ohdcha z-thr(allo,tbu)-ohdcha z-o-t-butyl-l-allo-threoninedicyclohexylammoniumsalt z-allo-thr(tbu)-oh o-(1,1-dimethylethyl)-n-[(phenylmethoxy)carbonyl]-l-allothreoninedicyclohexylammoniumsalt z-o-tert-butyl-l-allo-threoninedicyclohexylammoniumsalt Z-allo-Thr(tBu)-OH.DCHA

    Molecular Formula: C28H46N2O5

    Molecular Weight: 490.68

    MDL Number: MFCD00237372

    Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Chiral Intermediates

    Product Description:
    (L)-(1S,2S)-N-(benzyloxycarbonyl)-O-tert-butylthreonine dicyclohexylamine salt is a protected derivative of the non-proteinogenic amino acid L-allo-threonine. Its structure features a benzyloxycarbonyl (Cbz) group protecting the amine functionality and a tert-butyl group protecting the side-chain hydroxyl group, with the molecule existing as a dicyclohexylamine (DCHA) salt to enhance stability and handling properties. The compound possesses two chiral centers in the (1S,2S) configuration, making it a valuable chiral building block. This compound is primarily employed as a key chiral intermediate in the synthesis of complex bioactive molecules, particularly in pharmaceutical research. Its main application is in the preparation of peptide-based drugs and peptidomimetics, where the protected L-allo-threonine residue is incorporated to modulate the biological activity, stability, or pharmacokinetic properties of the target compound. The specific stereochemistry (allo-configuration) is crucial for achieving the desired interaction with biological targets. The DCHA salt form improves the compound's crystallinity and facilitates purification processes. As a protected amino acid derivative, it is a standard reagent in solid-phase peptide synthesis (SPPS) and solution-phase peptide chemistry, allowing for selective deprotection and further coupling reactions.
    Physical Properties
    mg g kg ml l t