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

2,3,5-Tri-O-acetyl-β-D-arabinofuranosyl fluoride is a chemically synthesized fluorinated sugar derivative of β-D-arabinofuranose. In this compound, the hydroxyl groups at positions 2, 3, and 5 are protected by acetyl groups, and the anomeric hydroxyl is substituted with a fluorine atom, forming a glycosyl fluoride in the β-configuration. This white crystalline solid is an important intermediate and glycosyl donor in synthetic carbohydrate chemistry due to its stability and reactivity. The fluorine substitution at the anomeric site imparts enhanced stability and allows controlled reactivity useful for regio- and stereoselective glycosylation reactions essential in oligosaccharide and glycoconjugate synthesis. With a molecular formula of C10H13FO8 and molecular weight approximately 268.20 g/mol, this compound is synthesized through acetylation and fluorination steps of arabinofuranosyl precursors. Produced under stringent synthetic and purification protocols, it offers high purity (≥95%) with minimal microbial contamination. Storage under refrigeration, protected from moisture and light, preserves its stability for over one year. Applications include enzymatic mechanism studies, glycomimetic development, drug design, and glycobiology research exploring arabinose-containing glycans.​IUPAC Name

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

Appearance

• White crystalline powder

Source

• Synthesized by peracetylation of arabinofuranose derivatives, followed by selective fluorination at the anomeric carbon
• Purified via chromatographic techniques to maintain high chemical quality and purity

Molecular Weight and Structure

• Molecular Formula: C10H13FO8
• Molecular Weight: 268.20 g/mol
• Structure: β-D-arabinofuranose ring with fluorine at C1 and acetyl protections at O2, O3, and O5
• Features key stereochemistry consistent with β-arabinofuranosyl fluorides used in glycosylation chemistry

Sugar Specificity

• β-D-arabinofuranosyl glycosyl donor with specificity driven by stereochemistry and substitution-level
• Facilitates selective glycosylation reactions for arabinose-containing oligosaccharides and glycoconjugates

Biological Activity

• No intrinsic biological activity; serves as a synthetic intermediate and enzyme substrate mimic
• Supports investigations in enzyme-specificity, substrate recognition, and glycosyltransferase mechanism

Purity and Microbial Contamination

• Typically supplied with purity ≥95%, verified by NMR and chromatography
• Chemical synthesis minimizes microbial contamination risk

Identity and Quality Control

• Identity confirmed by ^1H and ^13C NMR, fluorine NMR, MS, and HPLC purity analysis
• Batch Certificates of Analysis and SDS provided
• Melting point and optical rotation recorded for quality assurance

Shelf Life and Storage

• Store sealed at 2–8 °C, protected from moisture and light
• Stable for over 1 year under proper storage conditions

Application

• Key glycosyl donor in stereoselective synthesis of arabinofuranosyl oligosaccharides
• Utilized in glycomimetic synthesis and carbohydrate-based drug design
• Supports enzymatic assays for glycosyltransferases and glycosidases recognition studies
• Enables synthesis of molecular probes for arabinose-related glycobiology

Key Characteristics

• Fluorinated β-D-arabinofuranoside with triacetyl protections
• CAS: 147429-80-9
• Molecular weight ~268.20 g/mol
• White crystalline powder with high purity
• Stable and reactive glycosyl donor with controlled stereochemistry
• Rigorous quality control with full characterization data
• Supplied and stored with stability guarantees

Citations

• Cymit Química product profile​
• PubChem compound data​
• ChemicalBook synthetic details​
• MedChemExpress reference
• PMC enzymology research articles​
• Sigma-Aldrich glycosyl donor catalogs​
• ScienceDirect glycosylation methodology​
• Patent documents on sugar derivatives
• Synthose chemical suppliers
• Research on glycosyltransferase substrates​