1,3,5-Tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

1,3,5-Tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose is a chemically synthesized modified sugar derivative where the 2-position hydroxyl group of α-D-arabinofuranose is replaced by a fluorine atom, and hydroxyl groups at positions 1, 3, and 5 are protected by benzoyl groups. This fluorinated, benzoylated sugar is a white crystalline solid serving as a key intermediate in synthetic carbohydrate chemistry and medicinal chemistry research. The introduction of fluorine at the 2-position provides increased metabolic stability and altered enzymatic reactivity, which is pivotal for the design of enzyme inhibitors, glycomimetics, and diagnostic agents. The benzoyl protecting groups facilitate selective reactivity and improve compound stability during synthesis. This compound is valuable in the development of fluorinated oligosaccharides, glycosyl donor precursors, and in biochemical studies of carbohydrate-protein interactions and glycosylation. It is supplied with high purity, confirmed identity, and enjoys stable shelf life under refrigerated conditions, making it suitable for research in chemical biology, drug discovery, and diagnostic probe development.

IUPAC Name

• (2S,3R,4R,5S)-2-fluoro-1,3,5-tris(phenylmethanone)oxolane

Appearance

• White crystalline solid

Source

• Synthesized from α-D-arabinofuranose derivatives via benzoylation and fluorination reactions under controlled chemical synthesis

Molecular Weight and Structure

• Molecular Formula: C26H21FO6
• Molecular Weight: 456.43 g/mol
• Structure: Five-membered furanose ring with benzoyl groups attached at C1, C3, and C5; fluorine substituted at C2
• SMILES: C1C@HOC(=O)c3ccccc3)OC(=O)c4ccccc4

Sugar Specificity

• Fluorinated derivative of α-D-arabinofuranose, falling under 2-deoxy-2-fluoro sugar class
• Used in research on furanose sugar metabolism and glycosyltransferase specificity

Biological Activity

• Functions as a probe and intermediate in the synthesis of fluorinated glycosides and glycomimetics
• Fluorine substitution modifies enzymatic recognition and stability, offering prospects for inhibitor development
• Supports studies related to carbohydrate-protein interactions and enzymatic pathways

Purity and Microbial Contamination

• Purity generally ≥95% confirmed by chromatographic and NMR analytical methods
• Chemical-grade purity minimizes microbial contamination risk

Identity and Quality Control

• Identity verified by NMR spectroscopy, mass spectrometry, and HPLC purity profiling
• Supplied with detailed Certificates of Analysis and safety data sheets
• Melting point and optical rotation reported for quality assurance

Shelf Life and Storage

• Store in sealed containers at 2–8 °C away from moisture and light
• Stable for minimum 1 year under proper storage conditions

Application

• Used as intermediate for preparation of fluorinated oligosaccharides and glycosylation donors
• Facilitates chemical biology research involving glycan-protein interactions and enzyme studies
• Supports synthesis of therapeutic glycomimetics and molecular imaging probes
• Assist in drug design targeting carbohydrate-processing enzymes and receptors

Key Characteristics

• 2-Deoxy-2-fluoro-α-D-arabinofuranose tri-benzoylated derivative
• CAS number: 147453-06-2
• Molecular weight: 456.43 g/mol
• White crystalline solid with high purity (>95%)
• Stable and well-characterized for synthetic and biological use
• Enables study of fluorinated sugar effects on metabolism and enzyme function
• Supplied with comprehensive analytical data and quality control certificates
• Important tool for glycoscience, medicinal chemistry, and diagnostics
• Suitable for long-term storage in controlled environments

Citations

• ChemicalBook product info
• Synthose fluorinated sugar derivatives
• PubChem molecular structure and CAS
• Sigma-Aldrich carbohydrate reagents
• MedChemExpress fluorinated glycosides
• ScienceDirect fluorosugar studies
• PMC articles on fluorinated carbohydrate probes
• Google Patents fluorinated sugar syntheses
• Glentham Life Sciences fluorinated sugar product
• BOC Sciences carbohydrate intermediates