Description

n-[(1R,2R)-2-(1-Pyrrolidinyl)Cyclohexyl]-N'-(2,3,4,6-Tetra-o-Acetyl-β-D-Glucopyranosyl)-Thiourea CAS NO 942939-99-3 is a sophisticated chiral thiourea derivative, engineered as a highly selective organocatalyst and a key intermediate in advanced organic synthesis. Its molecular architecture, featuring a cyclohexyl-pyrrolidine scaffold linked to a protected glucopyranosyl unit, provides unique stereochemical control for asymmetric transformations. This compound is essential for researchers and process chemists in pharmaceutical development and fine chemical manufacturing who require precise enantioselectivity.

Application

• Asymmetric Organocatalysis: Employed as a chiral hydrogen-bond donor catalyst for enantioselective reactions, including Michael additions, Mannich reactions, and acylations.
• Pharmaceutical Intermediate: Serves as a critical building block in the synthesis of complex, biologically active molecules, particularly glycosidase inhibitors and neuraminidase inhibitors.
• Carbohydrate Chemistry Research: Used in studies involving glycosylation, the synthesis of glycosyl donors/acceptors, and the development of glycomimetics.
• Chemical Biology Probe: Acts as a tool compound for investigating enzyme mechanisms, particularly those of glycosidases and transferases.
• Chiral Separation Aid: Can be utilized in the development of chiral stationary phases or selectors for analytical and preparative chromatography.
• Ligand for Metal Complexes: Potential use in forming chiral metal complexes for catalytic applications.

Basic Information

Item	Details
Product Name	n-[(1R,2R)-2-(1-Pyrrolidinyl)Cyclohexyl]-N'-(2,3,4,6-Tetra-o-Acetyl-β-D-Glucopyranosyl)-Thiourea
CAS No.	942939-99-3
Molecular Formula	C25H39N3O9S
Molecular Weight	557.66 g/mol
Synonyms	(1R,2R)-2-(Pyrrolidin-1-yl)cyclohexyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylcarbamimidothioate; N-[(1R,2R)-2-(Pyrrolidin-1-yl)cyclohexyl]-N'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiourea; Glucopyranosyl thiourea derivative; Chiral acetylated glucosyl thiourea; Organocatalyst 942939-99-3; Asymmetric thiourea catalyst; Tetraacetylglucosyl thiourea
EINECS	Contact for details

Quality Control

Our production of n-[(1R,2R)-2-(1-Pyrrolidinyl)Cyclohexyl]-N'-(2,3,4,6-Tetra-o-Acetyl-β-D-Glucopyranosyl)-Thiourea adheres to stringent quality protocols to ensure batch-to-batch consistency and high purity for research and development applications. Each lot is characterized by advanced analytical techniques, including HPLC, NMR, and chiral analysis, to confirm identity, purity, and enantiomeric excess. A comprehensive Certificate of Analysis (COA) detailing all specifications is provided with every shipment.

Storage

Preserve in a tightly closed container, protected from light. Store in a cool, dry place at a controlled room temperature (15-25°C). This compound is moisture-sensitive (hygroscopic); desiccants are recommended for long-term storage. Keep away from strong acids and bases.

Specification

Item	Specification
Appearance	White to off-white solid
Identification (IR)	Conforms to structure
Identification (NMR)	Conforms to structure
Purity (HPLC)	≥ 97.0%
Enantiomeric Excess (Chiral HPLC)	≥ 99.0%
Water Content (KF)	≤ 0.5%
Residual Solvents (GC)	Meets ICH guidelines

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