Benzyl (S)-(-)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate p-toluenesulfonic acid salt, CAS No. 77497-97-3

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77497-97-3

Catalog No. EBD39480

CAS 77497-97-3

Name Benzyl (S)-(-)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate p-toluenesulfonic acid salt

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Basic Information

Synonyms: (S)-1,2,3,4-Tetrahydro-3-isoquinoline-carboxylicacidbenzylesterPTSAsalt Benzyl(S)-()-1,2,3,4-tetrahydro-3-isoquinolinecarboxylatep-toluenesulfonicacidsalt (S)-3-benzyloxycarbonyl-1,2,3,4-tetrahydroisoquinoliniump-toluenesulfonate benzyl(S)-(-)-1,2,3,4-tetrahydroiso-quinolinecar S-1,2,3,4-tetrahydro-isoquinoline-3-carboxylicacidbenzylesterptsasalt Phenylmethyl(3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate?PTSA?SALT Phenylmethyl(3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylatePTSASALT Benzyl(S)-(-)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylatep-toluenesulfonicacidsalt Phenylmethyl(

Molecular Formula: C24H25NO5S

Molecular Weight: 439.52

MDL Number: MFCD00799478

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

Product Description:

(S)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acid benzyl ester p-toluenesulfonate is a chiral organic salt. It is a derivative of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic), where the carboxylic acid is protected as a benzyl ester and the amine is protonated and paired with a p-toluenesulfonate (tosylate) counterion. The compound features a stereogenic center in the (S)-configuration at the 3-position of the tetrahydroisoquinoline scaffold. This compound is primarily utilized as a key chiral building block or intermediate in pharmaceutical research and synthesis. The Tic moiety is a privileged structure in medicinal chemistry, often incorporated into peptide mimetics and peptidomimetic drugs to modulate biological activity, enhance metabolic stability, or induce specific conformational constraints. The (S)-enantiomer is particularly valuable for constructing molecules with defined stereochemistry. The benzyl ester serves as a common protecting group for the carboxylic acid, while the tosylate salt form enhances stability and crystallinity for handling and storage. Its main application lies in the synthesis of potential drug candidates, especially in the areas of central nervous system (CNS) agents, protease inhibitors, and other bioactive peptides. It is a specialized intermediate rather than a commodity chemical, highlighting its role in the development of chiral pharmaceuticals.

Physical Properties

Melting Point: 145-150 °C(lit.)

Boiling Point: 634.1 °C at 760 mmHg

Flash Point: 337.3 °C

Safety Information

Packing Level: III

Hazard Category: 9

Transport Codes: 3077

Analytical Data

Appearance: white crystalline