Phenyl β-D-thioglucopyranoside

Phenyl β-D-thioglucopyranoside is a synthetic thioglycoside derivative of β-D-glucopyranose where the anomeric oxygen is replaced by a sulfur atom bonded to a phenyl group. This structural modification enhances its resistance to enzymatic and chemical hydrolysis, making it a robust glycosyl donor and valuable intermediate in carbohydrate chemistry. The compound typically appears as a white crystalline solid with a molecular formula of C12H16OS and a molecular weight of approximately 208.32 g/mol. Synthesized by the thiolysis of protected glucose precursors with phenyl thiol, and purified chromatographically to achieve purity greater than 95%, it exhibits enhanced chemical stability. Its identity and purity are confirmed by NMR spectroscopy, mass spectrometry, and HPLC. The synthetic process ensures minimal microbial contamination. Phenyl β-D-thioglucopyranoside should be stored in sealed containers at 2–8 °C, protected from moisture and light, with a shelf life of 1–2 years. It serves as a glycosyl donor in stereoselective oligosaccharide synthesis, glycomimetic development, enzymatic assays, and molecular probe construction in glycobiology research.

IUPAC Name

• Phenyl 1-thio-β-D-glucopyranoside

Appearance

• White crystalline powder

Source

• Synthesized by thiolysis of protected β-D-glucopyranosyl derivatives with phenyl thiol
• Purified by chromatography to ensure high purity and consistency

Molecular Weight and Structure

• Molecular Formula: C12H16OS
• Molecular Weight: 208.32 g/mol
• Structure: β-D-glucopyranose ring with sulfur-linked phenyl group at anomeric carbon
• Thioglycosidic bond provides enhanced stability relative to O-glycosides

Sugar Specificity

• β-Anomeric stereochemistry of D-glucopyranose
• Used as a stable glycosyl donor in carbohydrate synthesis

Biological Activity

• No inherent pharmacologic effect
• Utilized as a substrate mimic and synthetic intermediate

Purity and Microbial Contamination

• Purity typically >95% confirmed by NMR and chromatography
• Synthesized under sterile conditions reducing microbial contamination risk

Identity and Quality Control

• Confirmed via ^1H and ^13C NMR, MS, and HPLC
• Comes with Certificates of Analysis and Safety Data Sheet
• Melting point and optical rotation provided for each batch

Shelf Life and Storage

• Store sealed at 2–8 °C
• Protect from moisture and light
• Maintains stability and purity for 1–2 years

Application

• Glycosyl donor for stereoselective synthesis of glycoconjugates and oligosaccharides
• Supports drug discovery and glycomimetic development
• Used in biochemical and enzymatic studies of glycosyltransferases and glycosidases
• Enables molecular probe design exploring carbohydrate interactions

Key Characteristics

• Phenyl-substituted β-D-thioglucopyranoside
• CAS Number: 13776-48-6
• Molecular Weight: 208.32 g/mol
• Stable, white crystalline compound with hydrolytic resistance
• Comprehensive analytical and quality assurance data available
• Suitable for refrigerated storage with extended shelf life
• Widely used in glycochemistry, medicinal chemistry, and glycobiology research

Citations

• Chemical supplier Cymit Química​
• PubChem database entry​
• Sigma-Aldrich product information​
• MedChemExpress glycosylation intermediates
• PMC biochemical studies
• ChemSpider chemical profile​
• Synthose synthetic carbohydrate library
• Patent literature on thioglycosides
• Thermo Fisher Scientific reagents
• ScienceDirect glycochemistry articles