Ethyl b-D-thiogalactopyranoside

Ethyl β-D-thioglucopyranoside is a chemically synthesized thioglycoside derivative where the anomeric oxygen of β-D-galactopyranose is replaced by a sulfur atom linked to an ethyl group. This modification imparts enhanced stability against hydrolysis compared to O-glycosides, making the compound a valuable glycosyl donor and synthetic intermediate in carbohydrate chemistry. It is a white crystalline powder with a molecular formula of C8H16OS and a molecular weight of about 168.28 g/mol. Produced via thiolysis of protected β-D-galactopyranosyl derivatives with ethyl mercaptan, it is purified by chromatographic methods to a purity typically above 95%. Analytical identification involves NMR, mass spectrometry, and chromatography. Its synthesis route and conditions ensure minimal microbial contamination. The compound should be stored sealed at 2–8 °C, protected from moisture and light, with a shelf life of 1–2 years. Applications include stereoselective oligosaccharide assembly, medicinal chemistry, molecular probe development, and glycobiology research related to carbohydrate-protein interactions and glycosylation processes.

IUPAC Name

• Ethyl 1-thio-β-D-galactopyranoside

Appearance

• White crystalline powder

Source

• Synthesized by thiolysis of protected β-D-galactopyranosyl precursors with ethyl mercaptan
• Purified via chromatographic techniques under controlled laboratory conditions to ensure purity and consistency

Molecular Weight and Structure

• Molecular Formula: C8H16OS
• Molecular Weight: 168.28 g/mol
• Structure: β-D-galactopyranose ring with sulfur substituting anomeric oxygen, bonded to ethyl group
• SMILES: CCOC1OC(CO)C(O)C(O)C1S

Sugar Specificity

• Preserves β-anomeric stereochemistry of D-galactopyranose
• Used as a stable glycosyl donor for selective synthetic transformations

Biological Activity

• Chemically stable intermediate with no direct pharmacological activity
• Functions as substrate mimic in enzymology and glycosylation research

Purity and Microbial Contamination

• High purity (≥95%) confirmed by NMR and chromatographic analysis
• Synthetic origin minimizes microbial contamination

Identity and Quality Control

• Identity confirmed by 1H and 13C NMR, mass spectrometry, and HPLC purity profiles
• Includes Certificates of Analysis and Safety Data Sheets
• Melting point and optical rotation data provided for batch consistency

Shelf Life and Storage

• Store in sealed containers under refrigeration at 2–8 °C
• Protect from moisture, light, and heat
• Stable with a typical shelf life of 1–2 years under recommended conditions

Application

• Used as a glycosyl donor in stereoselective synthesis of oligosaccharides and glycoconjugates
• Supports drug discovery and glycomimetic design
• Facilitates molecular probe development targeting carbohydrate recognition
• Used in enzymatic assays studying glycosidases and glycosyltransferases

Key Characteristics

• Thioglycoside analog of β-D-galactopyranose with ethyl substitution
• CAS Number: 2167-39-1
• Molecular Weight: 168.28 g/mol
• White crystalline solid, hydrolytically stable
• Resistant to enzymatic cleavage enhancing synthetic utility
• Comprehensive analytical data supports identity and quality assurance
• Extended stability under recommended storage conditions

Citations

• Cymit Química​
• PubChem​
• Sigma-Aldrich​
• MedChemExpress
• PMC enzymology articles
• ChemSpider​
• Synthose chemical catalog
• Patent Literature
• Thermo Fisher Scientific​
• ScienceDirect glycochemistry reviews​