Phenyl α-D-thiomannopyranoside

Phenyl α-D-thiomannopyranoside is a synthetic thioglycoside derivative of α-D-mannopyranose, where the anomeric oxygen is replaced by a sulfur atom linked to a phenyl group. This chemical modification imparts significant stability against hydrolytic and enzymatic cleavage, making it an essential glycosyl donor and intermediate in synthetic carbohydrate chemistry. The compound appears as a white crystalline solid with a molecular formula of C12H16OS and molecular weight about 208.31 g/mol. It is synthesized by the reaction of phenyl thiol with acetyl-protected α-D-mannopyranose precursors under controlled laboratory conditions, followed by purification through chromatographic methods to achieve purity ≥95%. The compound’s integrity and structure are confirmed using NMR spectroscopy, mass spectrometry, and chromatography techniques, ensuring minimal microbial contamination. Storage in sealed containers at 2–8 °C, protected from moisture and light, maintains its stability for 1–2 years. Applications of phenyl α-D-thiomannopyranoside include its use as a glycosyl donor for stereoselective synthesis of mannose-containing oligosaccharides, glycomimetics, enzyme assays for carbohydrate-processing enzymes, and molecular probes in glycobiology studies.​

IUPAC Name

• Phenyl 1-thio-α-D-mannopyranosid

Appearance

• White crystalline powder

Source

• Prepared by phenyl thiolysis of acetylated α-D-mannopyranose derivatives
• Purified via chromatographic separation under laboratory synthesis conditions

Molecular Weight and Structure

• Molecular Formula: C12H16OS
• Molecular Weight: 208.31 g/mol
• Structure: α-D-mannopyranose ring with sulfur atom at anomeric carbon bonded to phenyl group
• Thioglycoside bond confers chemical and enzymatic stability

Sugar Specificity

• Retains α-stereochemistry of D-mannopyranose
• Functions as a stereochemically defined glycosyl donor

Biological Activity

• Not directly biologically active
• Used extensively in synthetic carbohydrate chemistry and enzymology as a glycosyl donor and substrate analog

Purity and Microbial Contamination

• Purity >95% confirmed by NMR and chromatography
• Synthetic origin reduces microbial contamination significantly

Identity and Quality Control

• Characterized by proton and carbon NMR, mass spectroscopy, and HPLC
• Provided with Certificates of Analysis (COA) and Safety Data Sheets (SDS)
• Batch-specific melting point and optical rotation recorded for quality assurance

Shelf Life and Storage

• Store sealed at 2–8 °C
• Protect from moisture, heat, and light
• Stable for 1–2 years under proper storage conditions

Application

• Used as glycosyl donor in stereoselective synthesis of mannose-containing oligosaccharides and glycoconjugates
• Supports drug discovery efforts in glycomimetic and carbohydrate-based therapeutics
• Employed in biochemical assays and molecular probe design targeting mannose-specific carbohydrate-binding proteins

Key Characteristics

• Phenyl-substituted α-D-thiomanopyranoside glycosyl donor
• Molecular weight: 208.31 g/mol
• White crystalline solid with high purity and chemical stability
• Resistant to hydrolysis and enzymatic cleavage
• Comprehensive analytical characterization and quality documentation
• Stable under recommended refrigerated storage
• Widely utilized in synthetic glycochemistry and medicinal chemistry

Citations

• Cymit Química synthetic product data​
• PubChem compound profile​
• Sigma-Aldrich reagent catalog​
• MedChemExpress chemical intermediates
• PMC glycoscience research articles
• ChemSpider molecular information​
• Synthose synthetic carbohydrate intermediates
• Patent literature on thioglycosides
• Thermo Fisher chemical reagents
• ScienceDirect synthetic glycobiology reviews