1,3,4,6-Tetra-O-acetyl-2-deoxy-2-fluoro-D-galactopyranose

1,3,4,6-Tetra-O-acetyl-2-deoxy-2-fluoro-D-galactopyranose is a fluorinated, acetyl-protected sugar derivative where the D-galactopyranose molecule is modified by replacing the hydroxyl group at position 2 with fluorine and acetylating hydroxyl groups at positions 1, 3, 4, and 6. This compound is a white crystalline solid, widely employed in synthetic carbohydrate chemistry and medicinal research for its ability to mimic natural sugar substrates with enhanced metabolic stability due to fluorine incorporation. The fluorine atom at C-2 changes the compound’s enzymatic reactivity and interaction profile, making it a valuable tool for investigating glycosylation pathways, enzyme mechanism studies, and glycomimetic drug development. Acetylation increases lipophilicity and facilitates manipulation in synthetic routes. The compound is supplied with high purity and quality assurance and is pivotal in the synthesis of fluorinated glycoconjugates and labeled diagnostic agents through bioorthogonal reactions.

IUPAC Name

• (2S,3R,4R,5R,6R)-2-fluoro-1,3,4,6-tetra-O-acetyl-D-galactopyranose

Appearance

• White crystalline powder

Source

• Synthesized chemically by selective fluorination and acetylation of D-galactose derivatives

Molecular Weight and Structure

• Molecular Formula: C14H19FO9
• Molecular Weight: 352.29 g/mol
• Structure: D-galactopyranose ring tetraacetylated at C1, C3, C4, C6 with a fluorine atom substituting the hydroxyl at C2
• SMILES: CC(=O)O[C@H]1OC(OC(C)=O)C@@HC@H[C@H]1OC(C)=O

Sugar Specificity

• Fluorinated galactose derivative acting as a substrate or inhibitor analogue in glycosylation studies
• Allows probing of enzyme specificity and glycan interactions

Biological Activity

• Functions as a probe in enzymatic activity and glycan recognition studies
• Fluorine confers resistance to enzymatic cleavage and modifies interaction with glycosyltransferases
• Used in drug design for fluorinated glycomimetics with improved stability

Purity and Microbial Contamination

• Typically ≥98% purity confirmed by NMR and HPLC
• Chemically pure, negligible microbial contamination through synthesis and purification

Identity and Quality Control

• Verified by nuclear magnetic resonance spectroscopy (NMR), mass spectrometry (MS), and chromatographic methods
• Certificate of Analysis and comprehensive safety data sheets supplied
• Melting point and optical rotation documented for quality assurance

Shelf Life and Storage

• Store in airtight containers at 2–8 °C
• Protect from moisture, heat, and light to prevent degradation
• Stable for 1–2 years under proper storage conditions

Application

• Precursor in synthesis of fluorinated glycosides and labeled imaging agents
• Used in studies on enzymatic mechanisms, metabolic pathway interrogation, and glycomimetic research
• Facilitates design of drug candidates and diagnostic tools targeting sugar-mediated biological processes

Key Characteristics

• Tetra-O-acetylated 2-deoxy-2-fluoro β-D-galactopyranose
• CAS number: 101561-17-4
• Molecular weight: 352.29 g/mol
• White crystalline solid with high purity (≥98%)
• Stable and versatile intermediate for synthetic and biochemical applications
• Verified identity and purity through rigorous characterization
• Critical for studies of fluorinated glycomimetics, enzymology, and molecular imaging
• Supplied with Certificates of Analysis and full QC documentation
• Supports broad research in glycoscience, medicinal chemistry, and diagnostics

Citations

• Synthose product info
• CymitQuimica catalog
• PubChem molecular data
• ChemicalBook descriptive information
• Sigma-Aldrich acetylated sugar catalog
• PMC enzymology and fluorosugar research
• ScienceDirect PET probe synthesis and stability study
• MedChemExpress fluorosugar intermediates
• AMC publications on fluorinated glycomimetics
• Quality control and analytical data