Methyl α-D-fucopyranoside

Methyl α-D-fucopyranoside is a synthetic derivative of the naturally occurring sugar L-fucose, where the anomeric hydroxyl group is replaced by a methyl group in the α-configuration of the pyranose ring. This compound is characterized by its white crystalline solid form and is widely used as a stable glycoside intermediate in carbohydrate chemistry. The methylation confers resistance to mutarotation and improves stability, making it suitable for glycosylation reactions and synthesis of functional glycoconjugates, oligosaccharides, and glycomimetics. With the molecular formula C7H14O5 and a molecular weight of approximately 178.18 g/mol, methyl α-D-fucopyranoside retains the sugar specificity of D-fucose but in a non-reducing form. It is produced through acid-catalyzed glycosylation with methanol, purified to high purity (≥98%), and validated by NMR and chromatographic methods. Produced under controlled, sterile conditions, it shows minimal microbial contamination. Proper storage at cool, dry, and dark conditions extends its shelf life up to two years. Applications include biochemical assays, medicinal chemistry, and glycobiology research focused on molecular recognition, enzyme specificity, and drug design.​

IUPAC Name

• Methyl α-L-fucopyranoside

Appearance

• White crystalline powder

Source

• Synthetically produced through acid-catalyzed glycosylation of D-fucose with methanol under laboratory conditions
• Purified via chromatographic methods ensuring chemical-grade quality

Molecular Weight and Structure

• Molecular Formula: C7H14O5
• Molecular Weight: 178.18 g/mol
• Structure: α-D-fucopyranose ring methylated at the anomeric oxygen; characteristic methyl ether and free hydroxyl groups​
• SMILES: CO[C@@H]1C@HC

Sugar Specificity

• Stereospecific for α-D-fucopyranose
• Recognized in carbohydrate-protein interactions and enzymatic processes involving fucose residues

Biological Activity

• Functions primarily as an intermediate; used in enzyme substrate and inhibitor studies
• Facilitates research on fucose-related glycosylation and glycoconjugates
• Not pharmacologically active per se but critical in drug development frameworks

Purity and Microbial Contamination

• Purity ≥98%, confirmed by NMR and chromatography
• Produced through aseptic chemical synthesis minimizing contamination

Identity and Quality Control

• Verified using NMR (1H, 13C), MS, and HPLC techniques
• Accompanied by Certificates of Analysis and Safety Data Sheets
• Melting point and optical rotation values recorded for consistency

Shelf Life and Storage

• Store sealed at 2–8 °C
• Protect from moisture, light, and heat to maintain stability
• Shelf life roughly 1–2 years when stored appropriately

Application

• Used as a synthetic intermediate in oligosaccharide and glycoconjugate synthesis
• Essential for biochemical assays targeting fucose-recognizing enzymes
• Supports medicinal chemistry and molecular probe design relating to fucosylated glycans
• Valuable in glycobiology research and drug discovery involving carbohydrate motifs

Key Characteristics

• Methylated α-D-fucopyranoside with high stereospecific purity
• CAS number: 5802-73-3
• Molecular weight: 178.18 g/mol
• White crystalline solid, chemically stable
• Enables regio- and stereoselective glycosylation
• Rigorous quality control with full analytic documentation
• Stable under recommended refrigerated storage
• Widely used in synthetic, biochemical, and pharmaceutical carbohydrate research

Citation Links

• AnaxLab compound profile​
• CalpacLab chemical catalog
• PubChem molecular database
• Sigma-Aldrich glycoside reagents​
• MedChemExpress biochemical substrates
• PMC research articles on glycobiology​
• Synthose synthetic intermediates
• Patent literature on fucose derivatives
• Scientific supplier Benchchem​
• ScienceDirect reviews on carbohydrate chemistry