(S)-2-benzyloxycarbonylamino-succinic acid 4-tert-butyl ester, CAS No. 5545-52-8

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5545-52-8

Catalog No. EBD50163

CAS 5545-52-8

Name (S)-2-benzyloxycarbonylamino-succinic acid 4-tert-butyl ester

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Basic Information

Synonyms: Z-Asp(OtBu)-OH.H2O 4-tert-ButylhydrogenN-((phenylmethoxy)carbonyl)-L-aspartate (2S)-2-{[(benzyloxy)carbonyl]amino}-4-tert-butoxy-4-oxobutanoicacid(non-preferredname) N-Benzyloxycarbonyl-L-asparticacid4-tert-butylester N-Cbz-L-Asparticacid4-tert-butylester Cbz-L-asparticacid4-tert-butylester Z-Asp(OtBu)-OH·H2O Z-Asp(OtBu)-OH N-Cbz-Asp(OtBu)-OH (S)-2-benzyloxycarbonylamino-succinicacid4-tert-butylester

Molecular Formula: C16H21NO6

Molecular Weight: 323.34

MDL Number: MFCD00042857

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Drug Synthesis Building Blocks Medicinal Chemistry > Biochemicals and Life Science Reagents > Amino Acids and Derivatives

Product Description:

(S)-2-Benzyloxycarbonylamino-succinic acid 4-tert-butyl ester is a protected derivative of L-aspartic acid. It features a benzyloxycarbonyl (Cbz) group protecting the α-amino group and a tert-butyl ester protecting the β-carboxylic acid side chain. This specific protection pattern is crucial for its primary application. This compound serves as a key chiral building block in the synthesis of peptides and peptidomimetics. The Cbz group is a widely used amine protecting group in peptide chemistry, while the tert-butyl ester offers orthogonal deprotection conditions, allowing for selective manipulation during multi-step syntheses. It is particularly valuable for introducing the L-aspartic acid residue into peptide sequences while preventing unwanted side reactions at the reactive β-carboxyl group. As a protected amino acid derivative, it is a fundamental reagent in medicinal chemistry research for constructing biologically active molecules, including potential drug candidates and enzyme inhibitors. Its high purity and defined stereochemistry are essential for ensuring the fidelity of the final synthetic targets.

Physical Properties

Boiling Point: 513.1 °C at 760 mmHg

Flash Point: 264.1 °C

Density: 1.219 g/cm3

Storage: −20°C

Analytical Data

Appearance: White powder