2,6-Dideoxy-2-fluoro-L-galactopyranose triacetate
[CAS# 188783-78-0]

Identification

• Classification: Biochemical >> Inhibitor >> Epigenetics >> Sirtuin inhibitor
• Name: 2,6-Dideoxy-2-fluoro-L-galactopyranose triacetate
• Synonyms: [(2S,3R,4R,5S)-4,6-diacetyloxy-5-fluoro-2-methyloxan-3-yl] acetate
• Molecular Formula: C₁₂H₁₇FO₇
• Molecular Weight: 292.26
• CAS Registry Number: 188783-78-0
• SMILES: C[C@H]1[C@H]([C@H]([C@@H](C(O1)OC(=O)C)F)OC(=O)C)OC(=O)C

Properties

• Solubility: Slightly soluble (7.9 g/L) (25 ºC), Calc.^*
• Density: 1.25±0.1 g/cm³ (20 ºC 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2016 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302+H312+H332-H315-H319-H335
• Precautionary Statements: P260-P280-P301+P312

Discovory and Applicatios

2,6-Dideoxy-2-fluoro-L-galactopyranose triacetate is a fluorinated carbohydrate derivative. The synthesis and study of fluorinated sugars emerged in the mid-20th century as part of a broader effort to explore the effects of fluorine substitution on organic molecules. The unique properties of fluorine, such as its ability to enhance biological activity and metabolic stability, have made it a focus of medicinal chemistry. The main feature of the chemical structure is that the compound has a typical sugar six-membered pyranose ring with a fluorine atom at the 2-position of the sugar ring. The three acetate groups attached to the molecule enhance the stability and solubility of the molecule. It is a white to off-white crystalline solid that is soluble in organic solvents such as chloroform and acetone.

2,6-Dideoxy-2-fluoro-L-galactopyranose triacetate is used as a glycosyl donor in glycoside synthesis. Its reactivity enables the transfer of its sugar moiety to various acceptors to form glycosidic bonds that are essential for the construction of complex carbohydrates. The compound facilitates the synthesis of fluorinated sugar conjugates, which are valuable for studying carbohydrate-protein interactions, enzyme inhibition, and drug design. These modified sugars can mimic natural carbohydrates while providing enhanced properties.

Introduction of fluorine into sugar derivatives has been shown to enhance their biological activity. 2,6-Dideoxy-2-fluoro-L-galactopyranose triacetate is used to design potential antiviral and antibacterial agents by modifying the carbohydrate portion of the bioactive molecule. In medicinal chemistry, the compound is used in the synthesis of prodrugs. The acetyl group can be enzymatically removed in vivo, releasing the active drug. Fluorinated sugars are used to improve the pharmacokinetic properties of these prodrugs.

The compound can be used as a probe in metabolic studies, helping researchers track and analyze carbohydrate metabolism. The fluorine atom provides a detectable label that can be used in NMR and other spectroscopic techniques to study metabolic pathways. 2,6-Dideoxy-2-fluoro-L-galactopyranose triacetate is used in enzyme inhibition studies to help identify and characterize inhibitors of glycosidases and glycosyltransferases.

Fluorinated sugars, including 2,6-Dideoxy-2-fluoro-L-galactopyranose triacetate, are used in X-ray crystallography to determine the structure of carbohydrate-protein complexes. Fluorine substitution provides additional electron density that helps to elucidate the molecular structure. In NMR spectroscopy, the compound provides valuable insights into the conformational dynamics of carbohydrates. The fluorine atom affects the magnetic environment of the molecule, allowing for detailed structural analysis.

This compound is a versatile building block in synthetic chemistry for the construction of more complex carbohydrate molecules. Its reactivity and stability make it a convenient starting material for the synthesis of a wide range of sugar derivatives. In carbohydrate chemistry, the acetyl groups in 2,6-dideoxy-2-fluoro-L-galactopyranose triacetate act as protecting groups. These groups can be selectively removed, allowing for controlled functionalization of sugar rings.