1-Fluoro-2,3,4,6-tetra-O-acetyl-α-D-mannopyranose

1-Fluoro-2,3,4,6-tetra-O-acetyl-α-D-mannopyranose is a chemically engineered fluorinated sugar where a fluorine atom substitutes the anomeric hydroxyl at C1 of the α-D-mannopyranose molecule, and the hydroxyl groups at C2, C3, C4, and C6 are protected as acetates. This white to off-white crystalline compound is synthetically produced and primarily serves as a valuable precursor in carbohydrate and medicinal chemistry, particularly as an activated glycosyl donor in the synthesis of modified oligosaccharides, glycomimetics, and complex glycoconjugates. The presence of a fluorine atom at the anomeric position significantly enhances the compound’s reactivity in glycosylation reactions, makes the resulting glycosidic bond more resistant to enzymatic cleavage, and can facilitate the introduction of ^18F for radiolabeling in PET tracer development. It is also a tool for probing enzyme specificity and sugar-protein recognition. The compound is supplied in high purity with stringent analytical controls, supporting its longevity and reliability for laboratory research and pharmaceutical applications.

IUPAC Name

• 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl fluoride

Appearance

• White to off-white crystalline powder

Source

• Produced by fluorination of acetyl-protected D-mannopyranose under strictly controlled laboratory synthesis

Molecular Weight and Structure

• Molecular Formula: C14H19FO9
• Molecular Weight: 350.29 g/mol
• Structure: Six-membered mannopyranose ring, acetyl groups at C2–C6, fluorine at C1, alpha-configuration
• SMILES: CC(=O)O[C@H]1OC(COC@HC1OC(C)=O)(OC(C)=O)OC(C)=O

Sugar Specificity

• α-D-mannose derivative, fluorinated at the anomeric (C1) position, allowing for unique enzyme and glycosylation pathway studies

Biological Activity

• Used as a glycosyl donor or probe for glycosidic bond formation
• Fluorine at C1 stabilizes glycosyl intermediates in chemical and potentially biological assays
• May be a precursor in ^18F radiolabeling to develop PET probes

Purity and Microbial Contamination

• Purity typically ≥95–98% as confirmed by NMR/HPLC
• Synthesized under clean, controlled conditions to ensure minimal microbial or particulate contamination

Identity and Quality Control

• Verified by 1H, 13C, and 19F NMR, mass spectrometry, and chromatographic analysis
• Melting point 68–69 °C
• Certificate of Analysis provided by reputable suppliers

Shelf Life and Storage

• Store at 2–8 °C, away from moisture and light
• Stable for at least 1–2 years under recommended conditions
• Stores well in tightly sealed containers

Application

• Glycosyl fluoride donor for synthesis of modified oligosaccharides and glycoconjugates
• Intermediate in radiochemical labeling (PET, ^18F-FDG synthesis)
• Used in studies of enzyme catalysis, glycosidic bond formation, and molecular imaging agent development
• Valuable for probing sugar-protein and carbohydrate-enzyme interactions

Key Characteristics

• Anomeric fluorinated, tetra-acetyl-protected α-D-mannopyranose
• CAS: 2823-44-1; molecular weight 350.29 g/mol
• High chemical and physical stability; white/off-white crystals
• Excellent glycosyl donor reactivity and radiochemistry precursor
• Reliable for medicinal and synthetic carbohydrate chemistry
• Strict analytical and batch quality control standards
• Functions as a tool for radiopharmaceutical and chemical biology research

Citations

• ChemicalBook CAS and synthetic overview
• Sigma-Aldrich related acetyl-mannopyranose
• Alfa Chemistry product reference
• PubChem structure and descriptor
• TCIChemicals purity and appearance data
• Patents on fluorinated sugar use in PET chemistry
• ScienceDirect and PMC PET/F-FDG tracer syntheses
• MedChemExpress synthetic intermediate
• Academic synthesis papers and reviews on glycosyl fluorides
• Synthesis QC and stability notes in chemical patent literature