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

1,3,4,6-Tetra-O-acetyl-2-deoxy-2-fluoro-β-D-galactose is a chemically synthesized carbohydrate derivative where the hydroxyl groups at positions 1, 3, 4, and 6 of the β-D-galactopyranose ring are modified with acetyl groups, and the hydroxyl group at position 2 is replaced by a fluorine atom. This fluorinated sugar analog serves as a valuable tool in glycochemistry and medicinal chemistry research, particularly for exploring the role of fluorinated sugars in enzyme recognition, glycosylation pathways, and metabolic stability. The acetyl groups provide protection enhancing synthetic manipulations, while the 2-fluoro substitution mimics the natural sugar but with altered chemical and biological properties, increasing resistance to enzymatic breakdown. The compound is a white crystalline solid, supplied with high purity, and is utilized in the synthesis of fluorinated glycomimetics, biochemical probes, and potential drug candidates targeting carbohydrate-mediated biological processes. It plays a significant role in the design of site-specific inhibitors and imaging agents due to the fluorine atom acting as a bioisostere.

IUPAC Name

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

Appearance

• White crystalline powder

Source

• Synthesized via selective fluorination and acetylation of D-galactose derivatives in the laboratory

Molecular Weight and Structure

• Molecular Formula: C14H19FO9
• Molecular Weight: 352.29 g/mol
• Structure: Pyranose form of D-galactose, acetylated at positions 1, 3, 4, and 6 with a fluorine substituent at carbon 2
• SMILES: CC(=O)OC[C@H]1OC(OC(C)=O)C@@HC@H@H]1OC(C)=O

Sugar Specificity

• Fluorinated analog of β-D-galactose
• Used as a glycosyl transferase and glycosidase substrate analog to study carbohydrate-enzyme interactions

Biological Activity

• Functions as an enzyme inhibitor or probe due to fluorine’s electron-withdrawing effect and steric influence
• Useful in research targeting galactose-processing enzymes involved in cellular signaling and disease mechanisms
• Applied in drug design for developing glycomimetic inhibitors with improved metabolic stability

Purity and Microbial Contamination

• Typical purity ≥98% by chromatographic and spectral methods
• Chemically synthesized compound with negligible microbial contamination
• Supplied with full quality assurance and Certificate of Analysis

Identity and Quality Control

• Verified using NMR, mass spectrometry, HPLC, and elemental analysis
• Includes safety data sheets and detailed analytical documentation
• Melting point reported around 104–107 °C

Shelf Life and Storage

• Stable for 1–2 years when stored at 2–8 °C under dry, dark conditions
• Should be sealed tightly to prevent hydrolysis or decomposition

Application

• Intermediate in the synthesis of fluorinated glycosides, glycomimetics, and potential pharmaceutical agents
• Used in enzymatic assays to study galactosidase specificity and inhibitor design
• Enables investigation of carbohydrate-protein interactions involving galactose residues
• Supports development of molecular imaging and therapeutic agents targeting glycosylation

Key Characteristics

• Tetra-O-acetylated 2-fluoro-2-deoxy-β-D-galactose derivative
• CAS number 101561-17-4
• Molecular weight 352.29 g/mol, white crystalline powder
• High purity and thoroughly characterized for research use
• Fluorine substitution provides unique chemical and biological effects
• Stable under refrigerated conditions with appropriate storage
• Widely used in glycoscience, medicinal, and pharmaceutical chemistry
• Compatible with bioorthogonal and enzymatic investigations
• Supplied with comprehensive QC data and Certificates of Analysis

Citations

• Synthose product data
• CymitQuimica chemical catalog
• PubChem fluorinated sugar analog
• ChemicalBook acetylated sugar details
• Sigma-Aldrich fluorosugar reagents
• PMC enzymology and fluorosugar studies
• ScienceDirect PET labeling and fluorosugar research
• PubMed Central metabolic fluorosugar review
• Brieflands glycomimetic synthesis study
• ACS Publications fluorinated nucleosides