29332-85-2

Usage

Chemical class

Difluorinated sugars

Parent compound

Glucose

1,6-anhydro

The hydroxyl group at the 1-position is replaced by an oxygen atom, forming an anhydro ring.

2,4-dideoxy

The hydroxyl groups at the 2and 4-positions are absent.

2,4-difluoro

The hydrogen atoms at the 2and 4-positions are replaced by fluorine atoms.

Stereochemistry

β-D-glucopyranose

β-configuration

The hydroxyl group at the 1-position is on the opposite side of the ring compared to the hydroxymethyl group at the 5-position.

D-configuration

The chiral center at the 5-position has the R-configuration (clockwise orientation of the substituents).

Pyranose

The ring structure is six-membered (hexopyranose) with oxygen as the ring-forming atom.

Potential applications

Medicinal chemistry and drug development

Mimics natural sugars

Can be used as a substitute for natural sugars in biological systems.

Altered physicochemical properties

The difluoro substitutions provide unique properties that can be exploited in drug design.

Research interest

Carbohydrate chemistry

Unique structure

The combination of anhydro, dideoxy, and difluoro substitutions results in a novel structure.

Chemical synthesis

The synthesis of 1,6-Anhydro-2,4-dideoxy-2,4-difluoro-β-D-glucopyranose presents challenges and opportunities for developing new synthetic methods and strategies.

Upstream product

• 3868-03-9 1,6:2,3-dianhydro-β-D-mannopyranose 
• 3868-08-4 1,6:2,3-dianhydro-4-O-(4-toluenesulfonyl)-β-D-mannopyranose 
• 498-07-7 levoglucosan 
• 23643-29-0 1,6-anhydro-4-O-(4-toluenesulfonyl)-β-D-glucopyranose 
• 3868-05-1 1,6-anhydro-2-O-(4-toluenesulfonyl)-β-D-glucopyranose 
• 33557-13-0 1,6-anhydro-4-deoxy-4-fluoro-2-O-(4-toluenesulfonyl)-β-D-glucopyranose 
• 33557-14-1 1,6:2,3-dianhydro-4-deoxy-4-fluoro-β-D-mannopyranose 
• 20204-80-2 [(1R,2S,3S,4R,5R)-3-hydroxy-4-(p-tolylsulfonyl)-6,8-dioxabicyclo[3.2.1]oct-2-yl]-4-methylbenzenesulfonic acid 
• 6167-32-4 1,6:3,4-dianhydro-2-O-tosyl-D-galactose 

Downstream Products

• 29514-08-7 (1R,2S,4R,5R)-6,8-dioxabicyclo[3.2.1]octane-2,4-diol 

Relevant academic research and scientific papers

Synthesis of 2,3,4-Trideoxy-2,3,4-trifluoroglucose

There is an increasing interest in investigating how polyfluorination of carbohydrates modifies their physical and biological properties. An example that has caught much attention is 2,3,4-trideoxy-2,3,4-trifluoroglucose. Four syntheses of this compound have been reported, which are either low yielding or long (13 or more steps). We report a 6-step synthesis of 2,3,4-trideoxy-2,3,4-trifluoroglucose starting from levoglucosan. The solution-phase structure of an intermediate, 1,6-anhydro-2,4-dideoxy-2,4-difluoroallose, features a rare example of a bifurcated F···H(O)···F hydrogen bond and is compared to its crystal structure.

Skipped Fluorination Motifs: Synthesis of Building Blocks and Comparison of Lipophilicity Trends with Vicinal and Isolated Fluorination Motifs

Given there is an optimal lipophilicity range for orally bioavailable drugs, structural modifications applied in the drug development process are not only focused on optimizing bioactivity but also on fine-tuning lipophilicity. Fluorine introduction can b

Addressing the Structural Complexity of Fluorinated Glucose Analogues: Insight into Lipophilicities and Solvation Effects

In this work, we synthesized all mono-, di-, and trifluorinated glucopyranose analogues at positions C-2, C-3, C-4, and C-6. This systematic investigation allowed us to perform direct comparison of 19F resonances of fluorinated glucose analogues and also to determine their lipophilicities. Compounds with a fluorine atom at C-6 are usually the most hydrophilic, whereas those with vicinal polyfluorinated motifs are the most lipophilic. Finally, the solvation energies of fluorinated glucose analogues were assessed for the first time by using density functional theory. This method allowed the log P prediction of fluoroglucose analogues, which was comparable to the C log P values obtained from various web-based programs.

Exploring the Chemistry of Non-sticky Sugars: Synthesis of Polyfluorinated Carbohydrate Analogues of d-Allopyranose

There is a growing interest in the preparation of polyfluorinated carbohydrates. A limited number of fluorohexopyranosides have been used in biological investigations because of the synthetic challenge they present. Hence, we report the synthesis of fluor

Synthesis and Lipophilicity of Trifluorinated Analogues of Glucose

In this work, we have developed synthetic routes for novel trifluorinated glucopyranose analogues using a Chiron approach. This strategy used inexpensive levoglucosan as a starting material, and we achieved a microwave glycosylation method as a key step. All analogues adopted standard 4C1 glucopyranose conformations, and a gauche-gauche conformation for the fluoromethyl group (C5-C6 linkage) was ascertained for congeners with a fluorine atom at C-6. Finally, the lipophilicity of trifluorinated glucose analogues was assessed with a log P determination method based on 19F NMR spectroscopy.