Ethyl 2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside

Ethyl 2,3,4,6-tetra-O-benzyl-β-D-thiogalactopyranoside is a synthetic thioglycoside derivative of β-D-galactopyranose, where all hydroxyl groups at positions 2, 3, 4, and 6 are protected by bulky benzyl groups, and the anomeric oxygen is replaced by sulfur linked to an ethyl group. This compound appears as a white crystalline solid, employed extensively as a highly stable and reactive glycosyl donor in synthetic carbohydrate chemistry. The benzyl protections provide enhanced lipophilicity, improved solubility in organic solvents, and steric regulation, allowing selective and efficient glycosylation in oligosaccharide synthesis. Ethyl 2,3,4,6-tetra-O-benzyl-β-D-thiogalactopyranoside has a molecular formula C35H40OS5 and a molecular weight of approximately 604.84 g/mol. It is synthesized under controlled conditions and purified by chromatographic methods to achieve high purity (>95%), with minimal microbial contamination. The compound is provided with full identity confirmation through NMR and chromatography and requires storage in sealed containers at 2–8 °C, protected from moisture and light, maintaining stability and efficacy for 1–2 years. This thiogalactoside is utilized in glycomimetic development, drug design, enzymatic studies, and as a molecular probe in glycobiology research.​

IUPAC Name

• Ethyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside

Appearance

• White crystalline solid

Source

• Synthesized by benzylation of ethyl β-D-thioglucopyranoside using benzyl bromide and strong base, followed by purification via chromatography
• Produced under strict laboratory conditions limiting impurities and contamination

Molecular Weight and Structure

• Molecular Formula: C35H40OS5
• Molecular Weight: 604.84 g/mol
• Structure: β-D-galactopyranose ring with benzyl ether protections on O2, O3, O4, and O6; sulfur substituent at anomeric carbon connected to an ethyl group
• Benzyl groups impart lipophilicity and steric bulk, facilitating selectivity in glycosylation

Sugar Specificity

• β-D-galactopyranosyl thioglycoside with protected hydroxyls to ensure selective glycosyl donor function
• Mimics natural glycosidic linkages with increased stability against hydrolysis

Biological Activity

• Synthetic intermediate without inherent biological activity
• Key substrate analog for glycosylation, enzyme mechanism studies, and inhibitor development

Purity and Microbial Contamination

• Purity typically >95%, confirmed by NMR and chromatographic techniques
• Synthetic preparation and packaging maintain negligible microbial contamination

Identity and Quality Control

• Verified by detailed NMR (1H, 13C), MS, and HPLC purity profiles
• Supplied with Certificates of Analysis and Safety Data Sheets
• Includes melting point, optical rotation, and TLC data for batch integrity checking

Shelf Life and Storage

• Store sealed at 2–8 °C, away from moisture and light
• Stable under recommended storage, with a shelf life of 1–2 years

Application

• Used as a glycosyl donor in stereoselective synthesis of galactosides, oligosaccharides, and glycoconjugates
• Facilitates drug candidate synthesis, molecular probe formation, and glycobiological research
• Employed in development of enzyme inhibitors and carbohydrate-based diagnostics

Key Characteristics

• Benzyl-protected ethyl β-D-thiogalactopyranoside glycosyl donor
• Molecular weight 604.84 g/mol; CAS not broadly registered
• White crystalline, lipophilic, hydrolytically stable
• Supports selective synthetic carbohydrate reactions
• Full analytical characterization and quality documentation
• Stable for extended periods under refrigeration and dryness
• Widely used in glycochemistry and medicinal chemistry research

Citations

• Cymit Química chemical profile​
• PubChem compound data​
• Sigma-Aldrich glycosyl donor catalog​
• MedChemExpress glycomimetic intermediate
• Research literature on thioglycosides
• ChemSpider molecular data​
• Synthose synthetic carbohydrate intermediates
• Patent documents on thioglycoside derivatives
• Thermo Fisher glycosylation reagents​
• ScienceDirect reviews on synthetic glycochemistry