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    146684-74-4

    Catalog No. EBD3313713

    CAS 146684-74-4

    Name (3R)-3,4-dihydro-2,3(1H)-Isoquinolinedicarboxylic acid 2-(phenylmethyl) ester

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    Basic Information

    Synonyms: (3R)-3,4-dihydro-2,3(1H)-Isoquinolinedicarboxylicacid2-(phenylmethyl)ester Z-D-TIC-OH (R)-(-)-2-(BENZYLOXYCARBONYL)-1,2,3,4-TETRAHYDRO-3-ISOQUINOLINECARBOXYLICACID N-ALPHA-CARBOBENZOXY-D-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLICACID Z-D-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLICACID Z-D-[3R]-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLICACID Z-[3R]-1,2,3,4-TETRAHYDROISOQUINOLENE-3-CARBOXYLICACID (3R)-2-[(benzyloxy)carbonyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylicacid

    Molecular Formula: C18H17NO4

    Molecular Weight: 311.34

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

    Product Description:
    This compound is a chiral, non-proteinogenic amino acid derivative. Its core structure is based on the 1,2,3,4-tetrahydroisoquinoline (Tic) scaffold, with a carboxylic acid group at the 3-position and a carboxybenzyl (Cbz) protecting group on the nitrogen atom. The stereocenter at the 3-position is in the (R)-configuration. This compound is a crucial chiral building block in medicinal chemistry and peptide research. The tetrahydroisoquinoline carboxylic acid (Tic) moiety is a privileged structure found in numerous bioactive molecules, including peptide mimetics and enzyme inhibitors. The (R)-N-Cbz-Tic-OH derivative is specifically employed in the solid-phase and solution-phase synthesis of constrained peptides and peptidomimetics. It serves to introduce conformational rigidity and specific stereochemistry, which are essential for modulating biological activity, selectivity, and metabolic stability in drug candidates targeting various receptors and proteases. The Cbz group provides orthogonal protection for the amine functionality during peptide coupling steps, allowing for selective deprotection under mild hydrogenation conditions. Its primary application lies in the research and development of novel therapeutic agents, particularly in the fields of central nervous system disorders, oncology, and cardiovascular diseases, where peptide-based drugs and mimetics are actively explored.
    Physical Properties

    Boiling Point: 522.5°Cat760mmHg

    Flash Point: 269.8°C

    Density: 1.308g/cm3

    mg g kg ml l t