Ethyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-thiogalactopyranoside

Ethyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-thiogalactopyranoside is a chemically synthesized thioglycoside derived from β-D-galactopyranose. It features benzoyl protective groups at the 2 and 3 positions, a benzylidene acetal bridging the 4 and 6 positions, and an ethyl thiol substituent at the anomeric carbon in the β-configuration. This compound appears as a white crystalline solid with a high degree of purity and structural specificity. The combination of benzoyl and benzylidene protections imparts stability and solubility in organic media while controlling the regio- and stereoselectivity of glycosylation reactions. The sulfur substitution at the anomeric position provides robust thioglycoside functionality, making it valuable as a glycosyl donor in synthetic carbohydrate chemistry. Its molecular formula is C31H28O6S, with a molecular weight of approximately 540.62 g/mol. Synthesized via benzoylation and benzylidene acetal formation of protected ethyl β-D-thioglucopyranoside, it is purified by chromatographic methods and validated by NMR and chromatographic analyses, confirming purity above 95%. The synthetic origin ensures minimal microbial contamination. For optimal stability and prolonged shelf life of 1–2 years, it should be stored in a sealed container at 2–8 °C, shielded from moisture and light. This compound is widely used for stereoselective glycosylations, glycomimetic construction, drug discovery, and biochemical research on carbohydrate-protein interactions and enzymatic functions.

IUPAC Name

• Ethyl 2,3-di-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

Appearance

• White crystalline solid

Source

• Synthesized by selective benzoylation and benzylidene acetal formation of ethyl β-D-thioglucoside
• Purified by chromatography ensuring chemical quality and homogeneity

Molecular Weight and Structure

• Molecular Formula: C31H28O6S
• Molecular Weight: 540.62 g/mol
• Structure: β-D-galactopyranose ring with ethyl thioglycoside at C1, benzoyl esters at O2 and O3, benzylidene acetal spanning O4 and O6 positions
• Sterically hindered substituents promote regio- and stereoselective reactivity

Sugar Specificity

• α/β-Thioglycoside analog of β-D-galactopyranose, maintaining biological sugar stereochemistry
• Enables substrate-specific synthetic modifications and enzyme interaction studies

Biological Activity

• No direct pharmacological activity but serves as key intermediate for glycosylation and drug design
• Used in molecular probe development and enzyme mechanism determination

Purity and Microbial Contamination

• Purity >95%, confirmed by NMR and HPLC
• Manufactured to pharmaceutical-grade standards minimizing microbial contamination

Identity and Quality Control

• Confirmed by ^1H,^13C NMR, MS, HPLC purity, supported with COA and SDS
• Quality assured through melting point and optical rotation measurements

Shelf Life and Storage

• Stored in sealed containers at 2–8 °C
• Protected from moisture, light, and atmospheric contaminants
• Stable for 1–2 years under optimal storage conditions

Application

• Glycosyl donor in stereoselective synthesis of glycoconjugates and oligosaccharides
• Supports drug discovery via carbohydrates and glycomimetic scaffolds
• Used in biochemical studies of glycosyltransferases and glycosidase enzyme mechanisms
• Molecular probe synthesis for carbohydrate-protein interaction analysis

Key Characteristics

• Benzoylated and benzylidene-protected ethyl β-D-thioglucopyranoside
• Molecular weight: 540.62 g/mol
• White crystalline solid, high purity and hydrolytic stability
• Resistant thioglycoside donor with controlled regioselectivity
• Detailed analytical and stability data provided
• Suitable for advanced glycochemistry and medicinal chemistry applications
• Shelf life and storage conditions optimized for long-term stability

Citations

• Cymit Química product page
• PubChem molecular data
• Sigma-Aldrich glycosylation reagent catalog
• MedChemExpress advanced glycosylation intermediates
• Research literature on thioglycoside reactivity
• ChemSpider molecular profiles
• Synthose product information
• Patent literature on protected thioglycosides
• Thermo Fisher scientific reagents
• ScienceDirect glycoscience review articles