4-Methylphenyl β-D-thioglucopyranoside

4-Methylphenyl β-D-thioglucopyranoside is a synthetic thioglycoside derivative of β-D-glucopyranose, where the anomeric oxygen is replaced by sulfur, and the thiol group is linked to a 4-methylphenyl moiety. This compound typically appears as a white crystalline solid and serves as a valuable glycosyl donor and stable intermediate in carbohydrate chemistry. The β-configuration of the glucopyranose ring combined with the thioglycosidic linkage provides enhanced stability against hydrolysis compared to O-glycosides, enabling selective glycosylation reactions in synthetic chemistry. The molecular formula is C13H18OS5 and the molecular weight is approximately 282.42 g/mol. It is commonly produced through the reaction of 4-methylphenyl thiol with protected glucopyranose derivatives under controlled conditions, ensuring purity levels above 95%. The compound is typically free from microbial contamination due to its synthetic preparation and is supplied with rigorous analytical characterization, including NMR and chromatography. Recommended storage is in a sealed container at 2–8 °C, protected from moisture and light, with a shelf life of 1–2 years. 4-Methylphenyl β-D-thioglucopyranoside finds applications in synthetic glycosylation, drug development, molecular probe synthesis, and glycobiology studies aimed at understanding enzyme specificity and carbohydrate interactions.

IUPAC Name

• 4-Methylphenyl 1-thio-β-D-glucopyranoside

Appearance

• White crystalline powder

Source

• Synthesized via the reaction of 4-methylthiophenol with protected glucopyranose derivatives under anhydrous, controlled laboratory conditions
• Purified by chromatographic techniques to ensure high purity and reproducibility

Molecular Weight and Structure

• Molecular Formula: C13H18OS
• Molecular Weight: 246.34 g/mol
• Structure: β-D-glucopyranose ring with sulfur replacing the anomeric oxygen bonded to a 4-methylphenyl group
• SMILES: CC1=CC=C(SC2OC(CO)C(O)C(O)C2O)C=C1

Sugar Specificity

• β-D-glucopyranosyl thioglycoside maintaining the stereochemistry and ring conformation of glucose
• Acts as a glycosyl donor, resistant to hydrolysis for controlled synthesis

Biological Activity

• Stable synthetic intermediate, not biologically active by itself
• Utilized in enzyme activity assays, glycosidase inhibition studies, and glycobiology probes

Purity and Microbial Contamination

• Typically ≥95% purity verified by NMR and chromatographic purity analysis
• Industrial chemical synthesis minimizes the risk of microbial contamination

Identity and Quality Control

• Confirmed by 1H NMR, 13C NMR, MS, and HPLC
• Supplied with Certificates of Analysis, melting point, and optical rotation data
• Quality-controlled batches with validated physicochemical properties

Shelf Life and Storage

• Store in sealed containers, refrigerated at 2–8 °C
• Protect from moisture, light, and heat
• Expected 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 molecular probe design related to carbohydrate recognition
• Employed in biochemical studies of glycosyltransferases and glycosidases
• Facilitates creation of thioglycoside-based inhibitors and substrates

Key Characteristics

• 4-Methylphenyl thioglycoside derivative of β-D-glucopyranose
• CAS number: 17620-07-2
• Molecular weight: 246.34 g/mol
• White crystalline powder with high purity and chemical stability
• Useful glycosyl donor resistant to hydrolysis
• Fully characterized for identity and quality assurance
• Stable upon refrigerated storage with moisture control
• Widely used in synthetic carbohydrate chemistry and glycomics

Citations

• Cymit Química chemical info
• PubChem molecular data
• Sigma-Aldrich glycosyl donor product page
• MedChemExpress glycosylation reagent
• Scientific literature on thioglycosides
• ChemSpider database entry
• Synthose synthetic carbohydrate intermediates
• Patent documents for thioglycoside synthesis
• Thermo Fisher glycoside catalog
• ScienceDirect reviews on glycosylation chemistry