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

1-Fluoro-2,3,4,6-tetra-O-acetyl-α-D-mannopyranose (often called acetofluoro-α-D-mannose or 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl fluoride) is a protected, activated fluorosugar widely used as a glycosyl donor and synthetic intermediate in glycochemistry and glycobiology research. It is derived from D-mannose, in which all hydroxyl groups except the anomeric one are acetylated and the anomeric position is substituted by fluorine in the α-configuration, giving a highly reactive yet bench-stable glycosyl fluoride. The compound is typically supplied as a white to off‑white crystalline powder with high purity (≥98%) and is designed for use as a key building block in the synthesis of complex oligosaccharides, glycoconjugates, and radiotracer precursors (e.g., for FDG-related mannose chemistry via closely related intermediates). Acetyl protection enhances solubility in organic solvents and controls regio/stereoselectivity in glycosylation reactions, while the C1–F bond provides a tunable leaving group under Lewis acid catalysis. Synthesized under controlled conditions from per‑acetylated mannose derivatives, it is characterized and quality‑controlled by NMR and chromatographic methods, with recommended storage sealed, dry, at 2–8 °C to maintain integrity and shelf life for at least 1–2 years.

IUPAC Name

• 2,3,4,6-tetra-O-acetyl-1-deoxy-1-fluoro-α-D-manno-hexopyranose

Appearance

• White to off‑white crystalline powder or solid

Source

• Prepared by acetylation of D-mannose to give per‑acetylated mannose, followed by fluorination at the anomeric position (e.g., using HF/pyridine or other fluorinating systems) to introduce the α-fluoro glycosyl donor.

Molecular Weight and Structure

• Molecular formula: C14H19FO9
• Molecular weight: 350.29 g/mol
• Structure: D-mannopyranose ring; acetyl esters at O2, O3, O4, O6; fluorine atom at C1 in α-configuration forming a glycosyl fluoride.
• Example structural description: $(2R,3R,4R,5R,6R)$-2-(acetoxymethyl)-6-fluorotetrahydro-2H-pyran-3,4,5-triyl triacetate.

Sugar Specificity

• Derived from D-mannose and retains the stereochemistry of α-D-mannopyranose at all ring centers.
• Functions as an α-mannosyl donor in glycosylation reactions, enabling introduction of mannosyl residues with defined stereochemistry.

Biological Activity

• Not used as a direct therapeutic; serves as a synthetic precursor/intermediate.
• Related per‑acetylated mannose derivatives and mannose triflate intermediates are key precursors in the synthesis of 2‑deoxy‑2‑[1818F]fluoro-D-glucose (FDG), supporting PET radiotracer production.
• Useful in generating mannosylated structures for probing mannose-recognizing lectins and glycosidases after further transformations.

Purity and Microbial Contamination

• Commercial material typically specified at ≥98% purity by NMR/HPLC.
• Being a fully synthetic, low‑water organic solid, microbial contamination is negligible when manufactured and stored correctly.

Identity and Quality Control

• Identity confirmed by 11H and 1313C NMR, often with characteristic signals of acetyl methyl groups and anomeric carbon, plus MS for molecular ion at $m/z$ ≈ 350.
• Suppliers provide COA including assay, melting point (around 68–69 °C), and sometimes IR and elemental/computed data for batch verification.

Shelf Life and Storage

• Recommended storage: sealed, dry, at 2–8 °C.
• Protect from moisture and strong acids/bases to prevent acetate hydrolysis or glycosyl fluoride decomposition.
• Under proper storage, shelf life is typically at least 1–2 years (supplier specifications often “store 2–8 °C, sealed in dry conditions”).

Application

• Glycosyl donor for stereoselective formation of α- or β-mannosides under Lewis acid catalysis in oligosaccharide and glycoconjugate synthesis.
• Intermediate in routes to FDG precursors via related tetra‑O‑acetyl mannose and mannose triflate chemistry, important for radiopharmaceutical manufacturing.
• Tool compound in glycobiology to build mannosylated ligands, probes, and inhibitors for lectins and glycosidases.

Key Characteristics

• Protected α-D-mannosyl fluoride (glycosyl fluoride) with four acetyl groups.
• CAS 2823‑44‑1; molecular weight 350.29 g/mol; formula C14H19FO9.
• White to off‑white crystalline powder, purity typically ≥98%.
• Powerful mannosyl donor for synthetic glycosylation, compatible with many organic solvents.
• Links into established FDG precursor chemistry via per‑acetylated mannose and mannose triflate intermediates.
• Requires cool, dry storage at 2–8 °C with good stability under recommended conditions.

Citations

• ChemicalBook product and property data for 2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl fluoride (Acetofluoro-α-D-mannose).
• PubChem entry for 2,3,4,6-tetra-O-acetyl-1-deoxy-1-fluoro-α-D-gluco-hexopyranose (closely analogous glycosyl fluoride properties).
• Sigma-Aldrich data on 2,3,4,6-Tetra-O-acetyl-D-mannopyranose (parent protected mannose core).
• PubChem/Medline article on synthesis of mannose triflate precursor for FDG (mannose acylation context).
• ScienceDirect article on practical synthesis of 1,3,4,6-tetra-O-acetyl-2-O-triflate-β-D-mannopyranose (mannose derivative family).
• Watson/TCI information on 1,3,4,6-Tetra-O-acetyl-β-D-mannopyranose and related mannose building blocks.
• LGC and patent documents describing mannose triflate intermediate usage in FDG manufacture.
• PubChem entry for 2,3,4,6-Tetra-O-acetyl-D-mannopyranose (physical/chemical data).
• MedChemExpress and Alfa Chemistry listings for tetra‑O‑acetyl mannose derivatives used as synthetic intermediates.
• ChemicalBook/other supplier data for 1,3,4,6-Tetra-O-acetyl-2-deoxy-2-fluoro-D-mannopyranose as a related fluoromannose analog