A Di-O-Acetylated Fluoro-Azido Glucose Building Block for Medicinal Chemistry
This protected fluorinated amino sugar combines a C-6 azide with two O-acetyl groups. Its structure supports research on glycoconjugates, nucleoside analogues, molecular probes, and carbohydrate-based materials.
Selectively modified sugars provide starting points for developing new molecules at the intersection of medicinal chemistry and glycobiology. 2-Acetamido-6-azido-1,4-di-O-acetyl-2,3,6-trideoxy-3-fluoro-D-glucopyranose is a fluorinated amino sugar with several sites for selective modification.
Chemical information
• Chemical name: 2-acetamido-6-azido-1,4-di-O-acetyl-2,3,6-trideoxy-3-fluoro-D-glucopyranose
• Formula calculated from the named structure: C₁₂H₁₇FN₄O₆
• Calculated molar mass: 332.29 g/mol
• Classification: Fluorinated compound
Structural features
Fluorine at C-3 can affect the electronic distribution and preferred conformation of the sugar, and can change its interactions with enzymes or other biological targets. It also provides a way to investigate how fluorination influences chemical and metabolic stability.
The C-6 azide acts as a handle for copper-catalyzed azide–alkyne cycloaddition, allowing covalent attachment to molecules that bear an alkyne. The C-2 acetamido group is a motif found in amino sugars and can contribute to molecular recognition. The O-acetyl groups protect the hydroxyls at C-1 and C-4, allowing controlled deprotection or further derivatization later in a synthesis.
The 2,3,6-trideoxy scaffold has fewer free hydroxyl groups than glucose. These changes can affect polarity, lipophilicity, and membrane permeability.
Research applications
1. Conjugates and prodrug research
The azide can serve as a coupling site in experimental antibody–drug conjugates, small-molecule–oligonucleotide conjugates, PROTACs, and other bifunctional molecules. The sugar scaffold and fluorine substituent give researchers ways to investigate changes in solubility, targeting, metabolism, and pharmacokinetics in the resulting derivatives.
2. Carbohydrate and nucleoside analogue synthesis
This protected amino sugar can be explored as a precursor to fluorinated nucleoside analogues and related carbohydrate derivatives. The acetyl groups offer flexibility when planning glycosylation and chain extension in solid- or solution-phase synthesis. These routes can support screening of analogues in antiviral and oncology research.
3. Chemical biology and materials research
The azide allows attachment of reporters such as fluorophores or biotin for imaging, purification, and studies of carbohydrate metabolism or protein–carbohydrate interactions. The compound can also be explored as a precursor or monomer for fluorinated glycopolymers and other functional materials.
Conclusion
Site-specific fluorination, an azide handle, and acetyl protection make this compound a versatile synthetic intermediate. It offers a starting point for glycoconjugate synthesis, probe development, and studies of modified carbohydrate structures.
Prepared by KASONS. For research use only.