Ethyl 4,6-O-benzylidene-b-D-thiogalactopyranoside

Ethyl 4,6-O-benzylidene-β-D-thioglucopyranoside is a synthetic thioglycoside derivative of the β-D-galactopyranose ring in which the hydroxyl groups on positions 4 and 6 are protected by a benzylidene acetal, and the anomeric hydroxyl group is replaced by a thiol linked to an ethyl group. This white crystalline solid is known for its chemical stability and reactivity as a glycosyl donor in carbohydrate chemistry. Its protective benzylidene group offers regioselective shielding, while the thioglycosidic linkage enhances resistance to hydrolysis compared to conventional O-glycosides, making it valuable for stereoselective glycosylation reactions in the synthesis of complex oligosaccharides and glycoconjugates. The compound has a molecular formula of C19H24OS and a molecular weight of approximately 308.45 g/mol. Synthesized through benzylidene formation followed by ethyl thioglycosylation under strictly controlled conditions, it achieves high purity (>95%) and is free from significant microbial contamination. Analytical verification involves NMR, mass spectrometry, and chromatography. Storage in sealed containers at 2–8 °C, protected from moisture and light, ensures a shelf life of 1–2 years. Applications span medicinal chemistry, drug development, glycomimetic research, and as molecular probes in glycobiology.

IUPAC Name

• Ethyl 4,6-O-benzylidene-1-thio-β-D-galactopyranoside

Appearance

• White crystalline powder

Source

• Prepared by benzylidene acetal formation between hydroxyls at C4 and C6 of ethyl β-D-thioglucopyranoside
• Synthesized and purified under inert and anhydrous conditions to maintain chemical integrity

Molecular Weight and Structure

• Molecular Formula: C19H24OS
• Molecular Weight: 308.45 g/mol
• β-D-galactopyranose ring with benzylidene acetal protective group over O4 and O6, sulfur replacing anomeric oxygen bound to an ethyl group
• Enhanced lipophilicity and steric bulk from benzylidene protecting group

Sugar Specificity

• β-D-thiogalactoside, maintaining stereospecific sugar conformation
• Supports selective glycosylation with regio- and stereochemical precision

Biological Activity

• Functions as a synthetic intermediate; not inherently bioactive
• Critical for constructing stable bioactive glycoconjugates and enzyme inhibitors

Purity and Microbial Contamination

• Purity generally >95% verified by NMR, MS, and chromatographic assays
• Synthetic preparation prevents microbial contamination

Identity and Quality Control

• Confirmed with 1H and 13C NMR, mass spectrometry, and HPLC purity profiling
• Certificates of Analysis and SDS provide comprehensive QC information

Shelf Life and Storage

• Store in sealed containers, refrigerated at 2–8 °C
• Protect from moisture and light exposure
• Stable shelf life of 1–2 years

Application

• Glycosyl donor for stereoselective synthesis of thiogalactosides and related glycoconjugates
• Valuable in design of glycomimetics, molecular probes, and pharmaceutical agents
• Employed in enzymatic and mechanistic studies of carbohydrate-processing enzymes

Key Characteristics

• Ethyl-substituted β-D-thioglucopyranoside with 4,6-O-benzylidene protection
• Molecular weight: 308.45 g/mol
• White crystalline solid with high purity and chemical stability
• Exhibits resistance to hydrolysis and suitable for controlled glycosylation
• Proven quality assurance with full analytical documentation
• Stable when stored appropriately for extended duration
• Widely used in glycochemistry and drug development research

Citations

• Cymit Química chemical data
• PubChem molecular data
• Sigma-Aldrich glycosyl donor catalog
• MedChemExpress glycosylation reagents
• PMC literature on thioglycosides
• ChemSpider molecular information
• Synthose carbohydrate intermediates
• Patent literature
• Thermo Fisher glycosylation reagents
• ScienceDirect glycochemistry articles