Description

(2S,4S)-1-n-Cbz-4-Mercaptopyrrolidine-2-Carboxylic Acid Benzyl Ester is a high-purity, chiral pyrrolidine derivative featuring both a protected mercaptan (thiol) group and a carboxylic acid benzyl ester. This compound is a critical building block in advanced pharmaceutical synthesis, particularly for the development of protease inhibitors and other bioactive molecules where stereochemistry is paramount. It is primarily utilized by pharmaceutical R&D departments, contract research organizations (CROs), and fine chemical manufacturers engaged in peptide mimetic and drug discovery programs.

Application

• Key Intermediate in Drug Discovery: Serves as a crucial chiral scaffold for synthesizing potential therapeutic agents, especially protease inhibitors targeting diseases like HIV, HCV, and hypertension.
• Peptidomimetic Chemistry: Used to introduce constrained proline-like structures with a modifiable thiol side chain into peptide backbones to enhance metabolic stability and binding affinity.
• Ligand and Catalyst Development: Acts as a precursor for chiral ligands or organocatalysts used in asymmetric synthesis.
• Bioconjugation and Linker Chemistry: The protected thiol group can be deprotected for site-specific conjugation in antibody-drug conjugates (ADCs) or bioconjugation applications.
• Academic and Industrial Research: Employed in medicinal chemistry programs for structure-activity relationship (SAR) studies and library synthesis.
• Custom Synthesis: A starting material for the bespoke synthesis of more complex, target-specific molecules for preclinical development.

Basic Information

Product Name	(2S,4S)-1-n-Cbz-4-Mercaptopyrrolidine-2-Carboxylic Acid Benzyl Ester
CAS No.	1176446-09-5
Molecular Formula	C21H23NO4S
Molecular Weight	385.48 g/mol
Synonyms	(2S,4S)-1-[(Benzyloxy)carbonyl]-4-mercaptopyrrolidine-2-carboxylic acid benzyl ester; (2S,4S)-1-Carbobenzoxy-4-mercaptopyrrolidine-2-carboxylic acid benzyl ester; (2S,4S)-1-Cbz-4-mercaptopyrrolidine-2-carboxylic acid benzyl ester; 1-N-Cbz-4-Mercapto-D-proline benzyl ester; (2S,4S)-4-Mercapto-1-[(phenylmethoxy)carbonyl]-2-pyrrolidinecarboxylic acid phenylmethyl ester; Benzyl (2S,4S)-1-[(benzyloxy)carbonyl]-4-sulfanylproline-2-carboxylate; (S,S)-1-Cbz-4-Mercaptoproline Bzl ester
EINECS	Contact for details

Quality Control

Our (2S,4S)-1-n-Cbz-4-Mercaptopyrrolidine-2-Carboxylic Acid Benzyl Ester is manufactured under strict quality management systems. Every batch undergoes comprehensive analytical testing, including chiral HPLC, to ensure high chemical and enantiomeric purity suitable for sensitive pharmaceutical research. A detailed Certificate of Analysis (COA) is provided with each shipment, documenting identity, purity, and impurity profiles.

Storage

Preserve in a tightly closed container, protected from light. Store under an inert atmosphere (e.g., nitrogen or argon) at 2-8°C to minimize oxidation of the thiol group and ensure long-term stability. Keep the container in a cool, dry, and well-ventilated area separate from strong oxidizing agents.

Specification

Item	Specification
Appearance	White to off-white solid
Identification (IR)	Conforms to structure
Identification (HPLC)	Conforms to reference
Purity (HPLC)	≥ 97.0%
Enantiomeric Purity (Chiral HPLC)	≥ 99.0% ee
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.