Ethyl 2,3,4,6-tetra-O-acetyl-β-D-thioglucopyranoside 

Ethyl 2,3,4,6-tetra-O-acetyl-β-D-thioglucopyranoside is a synthesized sulfur-containing analog of β-D-glucopyranoside, in which the hydroxyl groups at positions 2, 3, 4, and 6 are protected by acetyl groups, and the anomeric oxygen is replaced by a sulfur atom linked to an ethyl group. This modified thioglycoside appears as a white crystalline solid and serves as a versatile glycosyl donor in synthetic carbohydrate chemistry due to its enhanced stability against hydrolysis compared to O-glycosides. The compound has a molecular formula of C14H20O7S and a molecular weight of approximately 328.37 g/mol. It is produced via acetylation of ethyl β-D-thioglucopyranoside and purified by chromatographic methods ensuring high purity (>95%). The thioglycosidic linkage provides resistance to enzymatic cleavage, making this compound valuable in glycosylation reactions, oligosaccharide assembly, and drug design. It is supplied with rigorous analytical characterization, including NMR and mass spectrometry, and exhibits minimal microbial contamination due to synthetic preparation. Storage recommendations emphasize sealed containers at 2–8 °C, protection from moisture and light, supporting a shelf life of 1–2 years. Applications include glycosyl donor in chemical synthesis, medicinal chemistry, glycobiology, and molecular probe development for carbohydrate-related biological processes.

IUPAC Name

• Ethyl 2,3,4,6-tetra-O-acetyl-β-D-thioglucopyranoside

Appearance

• White crystalline powder

Source

• Synthesized by acetylation of ethyl β-D-thioglucopyranoside using acetic anhydride and pyridine under controlled conditions
• Purified through chromatography to achieve high purity and homogeneity

Molecular Weight and Structure

• Molecular Formula: C14H20O7S
• Molecular Weight: 328.37 g/mol
• Structure: β-D-glucopyranose ring acetylated at O2, O3, O4, O6, with sulfur at the anomeric position attached to an ethyl group
• SMILES: CCOC1OC(C(C(O1)SC)OC(C)=O)OC(C)=O

Sugar Specificity

• Thioglycoside analog of β-D-glucopyranose retaining stereospecificity required for enzymatic recognition studies and glycosylation control

Biological Activity

• Chemically stable intermediate lacking direct pharmacological activity
• Important for designing glycosidase-resistant glycoconjugates and molecular probes

Purity and Microbial Contamination

• Purity >95%, confirmed by NMR and chromatographic methods
• Produced under synthetic conditions limiting microbial contamination

Identity and Quality Control

• Confirmed by 1H NMR, 13C NMR, mass spectrometry, and HPLC purity profiling
• Supplied with Certificates of Analysis and Safety Data Sheets
• Includes melting point and optical rotation for batch verification

Shelf Life and Storage

• Recommended storage in sealed containers at 2–8 °C
• Protect from moisture, light, and heat
• Shelf life is approximately 1–2 years under ideal storage conditions

Application

• Used as a glycosyl donor in the stereoselective synthesis of oligosaccharides and glycoconjugates
• Supports medicinal chemistry and chemical biology research aimed at studying carbohydrate-protein interactions
• Facilitates development of drug candidates and molecular probes resistant to glycosidase activity
• Enables synthesis of thioglycoside-based enzyme inhibitors and substrates

Key Characteristics

• Ethyl β-D-thioglucopyranoside tetraacetate, thioglycoside donor
• CAS number: 21599-62-0
• Molecular weight: 328.37 g/mol
• White crystalline powder, high purity, hydrolytically stable
• Resistant to enzymatic cleavage compared to O-glycosides
• Comprehensive analytic and quality documentation included
• Stable for extended periods under refrigerated conditions
• Versatile intermediate in glycochemistry and drug discovery

Citations

• Cymit Química chemical data
• PubChem molecular information
• Sigma-Aldrich glycosylation reagents
• MedChemExpress carbohydrate intermediates
• Research articles on thioglycosides
• ChemSpider database entry
• Synthose chemical catalog
• Patent literature on thioglycoside synthesis
• Thermo Fisher glycoside catalog
• ScienceDirect synthetic glycochemistry reviews