2,3,5-Tri-O-acetyl-β-D-arabinofuranosyl fluorid

2,3,5-Tri-O-acetyl-β-D-arabinofuranosyl fluoride is a chemically synthesized carbohydrate derivative where the β-D-arabinofuranose sugar is protected by acetyl groups at positions 2, 3, and 5, and contains a fluorine atom at the anomeric carbon (C1) forming a glycosyl fluoride. It appears as a white crystalline solid and is employed extensively as a glycosyl donor in organic synthesis due to the high reactivity and stability of the glycosyl fluoride bond. This compound plays a critical role in synthetic carbohydrate chemistry by facilitating regioselective and stereoselective glycosylation of acceptors, essential for constructing complex oligosaccharides and glycoconjugates. Its fluorine substitution at the anomeric position provides enhanced stability against hydrolysis compared to other glycosides and allows fine control over reaction outcomes. The acetyl groups increase solubility and synthetic flexibility. With its high purity and verified identity, this compound is widely used in medicinal chemistry, glycobiology, and as an intermediate in drug development and bioconjugation studies.

IUPAC Name

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

Appearance

• White crystalline powder

Source

• Synthesized chemically via selective acetylation and fluorination of β-D-arabinofuranose derivatives under laboratory conditions

Molecular Weight and Structure

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

Sugar Specificity

• β-D-arabinofuranosyl fluoride derivative acetylated at 2,3,5 positions
• Utilized prominently for glycosylation reactions involving arabinofuranose sugars

Biological Activity

• Primarily a synthetic intermediate with no direct bioactivity
• The fluoride moiety offers predictive insights into glycosyltransferase enzyme behavior
• Plays a significant role in the design of glycosylated therapeutics and glycoconjugates

Purity and Microbial Contamination

• Supplier typically guarantees ≥95% purity confirmed by chromatographic and spectroscopic analysis
• Chemical synthesis and purification ensure minimal microbial contamination

Identity and Quality Control

• Analytically confirmed by detailed NMR (1H, 13C, 19F), MS, and HPLC purity data
• Melting point and optical rotation values provided as identity references
• Certificate of Analysis and Safety Data Sheets supplied with each batch

Shelf Life and Storage

• Store sealed under refrigeration at 2–8°C
• Protect from moisture and light to prevent degradation
• Stable for at least 1–2 years under recommended storage

Application

• Widely used as a glycosyl donor in chemical synthesis of oligosaccharides and glycoconjugates
• Supports enzymatic and chemical glycosylation research
• Utilized in developing glycomimetic drugs and targeted delivery systems
• Enables exploration of carbohydrate-protein interactions and enzyme mechanisms

Key Characteristics

• Acetylated β-D-arabinofuranosyl fluoride with triacetyl protection
• CAS number: 829531-64-0
• Molecular weight: 344.24 g/mol
• High purity crystalline solid with definitive spectral characterization
• Stable under refrigerated storage with protected conditions
• Important synthetic building block in glycoscience and medicinal chemistry
• Key intermediate for fluorinated sugar chemistry and bioorthogonal reactions
• Supplied with comprehensive QC protocols and Certificates of Analysis

Citations

• ChemicalBook compound info
• Sigma-Aldrich acetylated sugar catalog
• PubChem chemical and spectral data
• Synthose glycosyl fluoride products
• MedChemExpress fluorinated glycosides
• PMC articles on glycosylation and sugars
• ScienceDirect research on carbohydrate fluorides
• Patent literature on glycosyl fluoride synthesis
• Glyco-related research articles
• Quality control documentation in research compounds