Methyl 4-deoxy-4-fluoro-α-D-glucopyranoside

Methyl 4-deoxy-4-fluoro-α-D-glucopyranoside is a chemically synthesized fluorinated sugar derivative where the hydroxyl group at the 4-position of α-D-glucopyranoside is replaced by a fluorine atom, and the anomeric hydroxyl is methylated. This modification combines the stability of methyl glycosides with the unique properties imparted by fluorine substitution, such as altered electronic effects and enhanced metabolic stability. The compound typically appears as a white crystalline solid with high purity. It is valuable in glycochemistry and medicinal chemistry as a probe molecule for studying enzymatic mechanisms, glycosyltransferase specificity, and fluorinated glycomimetic drug development. The fluorine substitution can affect sugar recognition and enzyme binding, enabling medicinal chemists to design novel compounds with improved biological properties. Methyl 4-deoxy-4-fluoro-α-D-glucopyranoside is produced via stereoselective fluorination and methyl glycosylation of glucose derivatives, purified to ≥98% purity, and confirmed by spectral and chromatographic methods. It is synthesized under controlled conditions ensuring minimal microbial contamination. Optimal storage is recommended in a sealed container at 2–8 °C with protection from moisture and light, preserving the compound’s integrity for 1–2 years. Applications include synthetic carbohydrate chemistry, biochemical assay development, and therapeutic molecule design.

IUPAC Name:

• Methyl 4-deoxy-4-fluoro-α-D-glucopyranoside

Appearance:

• White crystalline powder

Source:

• Synthesized by fluorination of hydroxyl groups on methyl α-D-glucopyranoside derivatives, involving stereoselective chemical reactions and purification steps

Molecular Weight and Structure:

• Molecular Formula: C7H13FO5
• Molecular Weight: Approximately 208.17 g/mol
• Structure: α-D-glucopyranose ring with methyl group at anomeric carbon and fluorine substituent replacing the C4 hydroxyl

Sugar Specificity:

• Modified α-D-glucose with fluorine at C4, used for selective enzyme substrate analog studies and glycomimetic synthesis

Biological Activity:

• Useful as a probe molecule for understanding enzyme interactions affected by fluorine substitution; supports glycosyltransferase and hydrolase enzyme studies; facilitates design of fluorinated therapeutics

Purity and Microbial Contamination:

• Purity typically ≥98%, verified by NMR, HPLC, and chromatography; chemical synthesis minimizes microbial contamination

Identity and Quality Control:

• Identity confirmed by 1H and 19F NMR, MS, and HPLC analyses; COA and SDS provided by suppliers; melting point and optical rotation characteristics documented

Shelf Life and Storage:

• Store in tightly sealed containers at 2–8 °C
• Protect from moisture and light
• Stable for about 1–2 years under recommended conditions

Application:

• Serving as a fluorinated sugar analog for synthetic carbohydrate chemistry
• Used in medicinal chemistry for drug design and glycomimetic molecule synthesis
• Facilitates study of enzyme specificity and metabolic pathway modulation
• Widely applied in biochemical research and diagnostics

Key Characteristics:

• Methylated α-D-glucopyranoside with fluorine substitution at C4
• Molecular weight approx. 208.17 g/mol
• White crystalline, highly pure synthetic intermediate
• Supports enzymatic assays and medicinal chemistry applications
• Supplied with full analytical and quality guarantees
• Stable with proper refrigerated storage

Citation Links:

• AnaxLab chemical details
• ScienceDirect synthetic carbohydrate studies
• Sigma-Aldrich glycomimetic references
• PMC enzymology papers
• MedChemExpress synthetic probes
• Glentham Life Sciences catalog
• Patent literature for fluorosugar synthesis
• Synthose chemical supplier
• PubChem molecular information
• Chemistry Europe glycosylation research