Description

(2S,4S)-4-Azido-1,2-Pyrrolidinedicarboxylic Acid 1-(Phenylmethyl) Ester is a high-value, stereochemically defined azido-pyrrolidine derivative that serves as a critical chiral building block in advanced organic synthesis. Its core value lies in the reactive azido group and protected carboxylic acid functionality, enabling its use in click chemistry and peptide-mimetic scaffold construction. This compound is essential for research and development chemists in the pharmaceutical and biotechnology sectors, particularly for the synthesis of novel drug candidates, proteolysis-targeting chimeras (PROTACs), and complex bioactive molecules.

Application

• Pharmaceutical Intermediate: A key chiral synthon for the development of novel active pharmaceutical ingredients (APIs), especially those targeting protease inhibition or requiring constrained peptide backbones.
• PROTAC & Bifunctional Molecule Synthesis: Utilized in the construction of linkers and warhead components for Proteolysis-Targeting Chimeras (PROTACs) and other heterobifunctional degraders via copper-catalyzed azide-alkyne cycloaddition (CuAAC).
• Peptidomimetic & Macrocycle Chemistry: Serves as a constrained proline analog for designing peptide mimics with enhanced metabolic stability, bioavailability, and target selectivity.
• Chemical Biology Probe Development: Incorporated into activity-based probes (ABPs) and photoaffinity labels for studying enzyme function and protein-protein interactions.
• Material Science & Polymer Chemistry: Acts as a functional monomer for creating specialty polymers with tailored properties through post-polymerization modification via the azide group.
• Academic & Contract Research: Employed in academic laboratories and CROs (Contract Research Organizations) for methodological development in asymmetric synthesis and bioorthogonal chemistry.

Basic Information

Product Name	(2S,4S)-4-Azido-1,2-Pyrrolidinedicarboxylic Acid 1-(Phenylmethyl) Ester
CAS No.	1155262-85-3
Molecular Formula	C14H14N4O4
Molecular Weight	302.28 g/mol
Synonyms	(2S,4S)-4-Azidopyrrolidine-1,2-dicarboxylic acid 1-benzyl ester; 1-Benzyl (2S,4S)-4-azidopyrrolidine-1,2-dicarboxylate; (2S,4S)-1-(Benzyloxycarbonyl)-4-azidopyrrolidine-2-carboxylic acid; (2S,4S)-4-Azido-1-Cbz-pyrrolidine-2-carboxylic acid; Cbz-(2S,4S)-AHP-OH (Azido-Hydroxy-Proline derivative); (2S,4S)-4-Azido-N-Cbz-proline; Azido-Cbz-Pro-OH (stereospecific); Benzyl (2S,4S)-4-azidopyrrolidine-1,2-dicarboxylate
EINECS	Contact for details

Quality Control

Our (2S,4S)-4-Azido-1,2-Pyrrolidinedicarboxylic Acid 1-(Phenylmethyl) Ester is manufactured under strict quality management systems. Each batch undergoes comprehensive analytical testing, including chiral HPLC to confirm stereochemical purity and identity verification by spectroscopic methods. We provide a detailed Certificate of Analysis (COA) with each shipment, ensuring traceability and compliance with your research or cGMP (current Good Manufacturing Practice) requirements for early-phase development.

Storage

Preserve in a tightly closed container, protected from light. Store in a cool, dry place at a controlled room temperature (15-25°C). Due to its light-sensitive nature and reactive azide functionality, prolonged exposure to light, heat, or moisture should be avoided. For long-term storage, consider storing under an inert atmosphere.

Specification

Item	Specification
Appearance	White to off-white solid
Identification (IR)	Conforms to structure
Identification (NMR)	Conforms to structure
Purity (HPLC)	≥ 97.0%
Chiral Purity (Chiral HPLC)	≥ 99.0% de
Water Content (KF)	≤ 0.5%
Residue on Ignition	≤ 0.1%

Note: Specifications can be tailored. Please contact us for the detailed technical data sheet of a specific grade.