1,2,4,6-Tetra-O-acetyl-3-deoxy-3-fluoro-D-glucopyranose

1,2,4,6-Tetra-O-acetyl-3-deoxy-3-fluoro-D-glucopyranose is a synthetic carbohydrate derivative where the D-glucopyranose ring carries acetyl groups at positions 1, 2, 4, and 6, with a fluorine atom substituting the hydroxyl group at position 3. This structural modification results in enhanced chemical stability and distinct biological behavior, making it an important compound in carbohydrate chemistry, especially for studies involving fluorinated sugar analogs that probe enzymatic processes and metabolic pathways. It is a white crystalline powder and serves as a critical intermediate in the synthesis of fluorinated glycoconjugates, fluorosugars used in drug development, and radiolabeled imaging agents. The acetyl groups aid solubility and synthetic versatility, while the fluorine substitution provides resistance to enzymatic degradation and affects interaction with carbohydrate-processing enzymes. Reliable for a range of applications in glycoscience, medicinal chemistry, and molecular imaging, it is supplied with high purity and comprehensive quality control.

IUPAC Name

• (2R,4R,5R,6R)-3-fluoro-1,2,4,6-tetra-O-acetyl-D-glucopyranose

Appearance

• White crystalline solid

Source

• Produced via chemical fluorination and acetylation of glucose derivatives under laboratory synthesis protocols

Molecular Weight and Structure

• Molecular Formula: C14H19FO9
• Molecular Weight: 352.29 g/mol
• Structure: Pyranose ring with acetyl groups at C-1, C-2, C-4, and C-6 positions; fluorine substitution at C-3 impacting the sugar’s stereochemistry and reactivity
• SMILES: CC(=O)O[C@H]1OC@@HC@HC@@H[C@H]1OC(C)=O

Sugar Specificity

• A fluorinated analog of D-glucopyranose, specifically modified at C-3
• Acts as a probe for enzymatic glycoside cleavage and glucosidase substrate specificity

Biological Activity

• Used to study inhibitory effects on carbohydrates-processing enzymes
• Fluorine substitution confers altered metabolic stability and resistance to enzymatic degradation
• Important in the design of glycomimetics and fluorinated carbohydrate drugs

Purity and Microbial Contamination

• Typically ≥98% purity as assessed by NMR and HPLC
• Microbial contamination is negligible due to synthetic nature and pharmaceutical-grade manufacturing

Identity and Quality Control

• Verified by NMR (1H, 13C, 19F), elemental analysis, MS, and chromatographic methods
• Supplied with Certificates of Analysis, safety data sheets, and spectral documentation

Shelf Life and Storage

• Stable for up to 2 years under refrigeration at 2–8 °C
• Protect from moisture, light, and heat
• Store in a dry, tightly sealed container to maintain integrity

Application

• Intermediary in synthesis of fluorinated glycosides and radiolabeled PET tracers
• Useful in enzymology studies as an inhibitor or substrate analog for glycosidases
• Facilitates research in glycoscience, drug design, and diagnostic imaging
• Supports development of fluorinated glycomimetic therapeutics and biochemical probes

Key Characteristics

• Tetra-O-acetylated 3-fluoro-3-deoxy-D-glucopyranose
• CAS number 363-83-5
• Molecular weight 352.29 g/mol, white crystalline solid
• High purity (≥98%) with comprehensive spectral characterization
• Stable under controlled refrigerated storage
• Offers mechanistic insights into enzyme-substrate specificity in glycosylation
• Crucial precursor for constructing fluorinated carbohydrates for clinical applications
• Supplied with full QC and COA for reliable research use
• Used widely in medicinal chemistry and molecular imaging development

Citations

• Synthose product info on 1,2,4,6-Tetra-O-acetyl-3-deoxy-3-fluoro-D-glucopyranose
• CymitQuimica chemical catalog and properties
• PubChem molecular data
• ChemicalBook fluorinated sugar derivatives
• Sigma-Aldrich glucose derivatives
• PMC studies on fluoroglycosides
• Scientific reports on PET tracer stability
• Research articles on fluorinated glycomimetics
• Brieflands quality control studies
• ScienceDirect related carbohydrate chemistry