2,3,5-Tri-O-acetyl-L-arabinofuranosyl fluoride

2,3,5-Tri-O-acetyl-L-arabinofuranosyl fluoride is a chemically synthesized derivative of the natural sugar L-arabinofuranose, featuring acetyl groups at positions 2, 3, and 5 and a fluorine atom substituting the anomeric hydroxyl group at carbon 1. This white crystalline compound is utilized extensively in synthetic carbohydrate chemistry, particularly as a highly reactive glycosyl donor in stereoselective glycosylation reactions. The fluorine atom at the anomeric position provides stability and enhanced reactivity, facilitating efficient glycosidic bond formation with precise stereochemical control. Acetyl protections increase the molecule’s solubility and synthetic stability, allowing facile manipulation by organic chemists. This compound serves as a critical intermediate in the development of complex oligosaccharides, glycoconjugates, and fluorine-labeled probes for medical diagnostics and therapeutic design. It is supplied in high purity with rigorous quality control parameters, and requires controlled storage to maintain its integrity for use in biochemical and pharmaceutical research.

IUPAC Name

• (2R,3R,4R,5R)-2,3,5-triacetyloxy-1-fluorooxolane

Appearance

• White crystalline solid

Source

• Synthesized chemically through selective acetylation and fluorination of L-arabinofuranose derivatives under controlled conditions

Molecular Weight and Structure

• Molecular Formula: C12H15FO8
• Molecular Weight: 344.24 g/mol
• Structure: Five-membered arabinofuranose sugar ring with acetyl groups on C2, C3, and C5, and fluorine substituent at the anomeric C1
• SMILES: CC(=O)O[C@@H]1C@@HC@HC@@HCO1

Sugar Specificity

• Fluorinated and acetylated analog of L-arabinofuranose
• Utilized for challenging glycosylations and synthesis of complex glycans involving arabinofuranose residues

Biological Activity

• Primarily acts as a synthetic intermediate and glycosyl donor
• Research utility in studying enzymatic mechanisms and glycosylation pathways involving L-arabinose-containing glycoconjugates
• Facilitates the creation of glycomimetics with fluorine-induced properties advantageous for medicinal chemistry

Purity and Microbial Contamination

• Typically supplied at ≥95% purity, confirmed by NMR and HPLC techniques
• Minimal to no microbial contamination due to rigorous chemical synthesis and purification protocols

Identity and Quality Control

• Verified by detailed NMR spectroscopy, chromatographic methods, and mass spectrometry
• Melting point and optical activity data included in quality documentation
• Certificate of Analysis and safety data sheets accompany the compound

Shelf Life and Storage

• Recommended storage at 2–8 °C in sealed, moisture-free containers
• Stable for at least 1–2 years when stored properly
• Avoid exposure to heat, moisture, and light to maintain chemical integrity

Application

• Critical glycosyl donor for chemical synthesis of arabinose-containing oligosaccharides
• Used in studies of enzyme specificity and glycosidic bond formation
• Supports synthetic glycomimetics, drug discovery, and molecular imaging research
• Enables conjugation reactions in chemical biology and bioorthogonal chemistry

Key Characteristics

• 2,3,5-Tri-O-acetylated 1-fluoro L-arabinofuranose
• CAS number: 27775-42-2
• Molecular weight: 344.24 g/mol
• White crystalline solid, high purity with established characterization
• Stable, reactive glycosyl fluoride for advanced synthetic applications
• Supports enzyme mechanism studies and glycan research
• Supplied with full quality assurance and analytical data
• Foundational reagent in glycobiology, medicinal chemistry, and chemical biology

Citations

• ChemicalBook product and molecular data
• Sigma-Aldrich product listing
• PubChem chemical structure and properties
• Synthose glycosyl fluoride reagents
• MedChemExpress fluorinated sugars
• PMC glycoscience articles
• ScienceDirect glycosylation research
• Patent literature on fluorinated sugar syntheses
• Glentham fluorinated sugar catalog
• BOC Sciences carbohydrate intermediates