1,3,4-Tri-O-acetyl-2-deoxy-2-fluoro-D-fucose

1,3,4-Tri-O-acetyl-2-deoxy-2-fluoro-D-fucose is a fluorinated, acetyl-protected derivative of D-fucose where the hydroxyl group at carbon 2 is replaced by a fluorine atom, and the hydroxyls at carbons 1, 3, and 4 are acetylated. This compound is a white crystalline solid that serves as a key intermediate in synthetic carbohydrate chemistry and glycobiology. The fluorine substitution at C2 enhances the sugar’s metabolic stability and alters enzymatic recognition properties, making it valuable in the design of glycomimetics, enzyme inhibitors, and molecular probes. Acetylation provides chemical stability and improves synthetic versatility. Its applications include drug design, study of carbohydrate-processing enzymes, glycan-protein interaction research, and as precursors for fluorinated glycoconjugates or radiolabeled imaging agents. This compound is supplied with high purity, thorough identity verification, and stable shelf life under appropriate storage conditions, facilitating wide use in medicinal chemistry and glycobiology.

IUPAC Name

• (2S,3S,4R,5R,6R)-2-fluoro-1,3,4-triacetyloxy-5-methylhexopyranose

Appearance

• White crystalline solid

Source

• Synthesized chemically by fluorination of acetyl-protected D-fucose precursors

Molecular Weight and Structure

• Molecular Formula: C12H17FO8
• Molecular Weight: ~334.25 g/mol
• Structure: D-fucose pyranose ring with acetyl groups at C1,3,4, fluorine substitution at C2
• SMILES: CC(=O)O[C@@H]1OC@@HC@HC@H[C@H]1C

Sugar Specificity

• Fluorinated analog of D-fucose, structurally modified at position 2
• Acts as a substrate analog for fucosyltransferases and glycosidases in enzymatic studies

Biological Activity

• Used in probing fucose-dependent glycosylation pathways and enzyme inhibition
• Valuable for the design of glycomimetic drugs with enhanced metabolic stability
• Facilitates research into immune recognition and microbial adhesion processes

Purity and Microbial Contamination

• High purity ≥97% confirmed by NMR and HPLC analysis
• Chemically pure, free from microbial contamination due to synthesis and high-grade purification

Identity and Quality Control

• Verified by NMR spectroscopy, mass spectrometry, and chromatographic purity assays
• Provided with Certificates of Analysis and detailed safety documentation
• Melting point and optical rotation values reported and verified

Shelf Life and Storage

• Store in a dry, cool place at 2–8 °C
• Stable for 1–2 years with minimal degradation under recommended storage
• Protect from moisture and light exposure

Application

• Synthetic intermediate in glycoscience and medicinal chemistry
• Used for producing fluorinated glycosides and glycomimetics for therapeutic research
• Employed in enzyme activity studies and inhibitor design targeting fucosyltransferases
• Supports development of imaging agents and drug delivery systems involving glycans

Key Characteristics

• Tri-O-acetylated 2-fluoro-2-deoxy-D-fucose derivative
• CAS number: 148648-15-4
• Molecular weight ~334.25 g/mol, white crystalline solid
• High purity and stable for long-term research use
• Versatile for chemical modification and biochemical studies
• Enables deeper understanding of fucosylation and glycosylation pathways
• Supplied with complete quality certification and analytical verification
• Role in drug discovery and diagnostic development across biomedical fields

Citations

• Synthose product details
• CymitQuimica chemical catalog
• ChemicalBook molecular and structural data
• PubChem fluorinated sugar analog
• Sigma-Aldrich acetylated sugar derivatives
• PMC biochemical studies on fluorosugars
• ScienceDirect PET probe investigations
• MedChemExpress fluorinated glycomimetics
• ACS publications related to fluorosugar research
• Quality control and stability reports