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Usage

Uses

Used in Medicinal Chemistry:
.beta.-D-Glucopyranose, 1,6-anhydro-2-deoxy-2-fluoro-4-O-(phenylmethyl)is used as a key compound in the development of new antiviral or antifungal agents. Its unique structure and chemical properties make it a promising candidate for creating novel therapeutics to combat various viral and fungal infections.
Used in Pharmaceutical Research:
.beta.-D-Glucopyranose, 1,6-anhydro-2-deoxy-2-fluoro-4-O-(phenylmethyl)is also utilized in pharmaceutical research to explore its potential biological activities and therapeutic uses. Further studies are necessary to fully understand its interactions with biological systems and to determine its efficacy and safety in treating specific medical conditions.
Used in Drug Delivery Systems:
In the field of drug delivery, .beta.-D-Glucopyranose, 1,6-anhydro-2-deoxy-2-fluoro-4-O-(phenylmethyl)may be employed to improve the delivery, bioavailability, and therapeutic outcomes of certain medications. Its unique structure could potentially enhance the targeting and release of drugs, making it a valuable tool in the development of advanced drug delivery systems.
Used in Chemical Synthesis:
Due to its complex molecular structure, .beta.-D-Glucopyranose, 1,6-anhydro-2-deoxy-2-fluoro-4-O-(phenylmethyl)can be used as a starting material or intermediate in the synthesis of other complex organic compounds. This makes it a valuable asset in the field of chemical synthesis, particularly for the creation of novel molecules with specific applications in various industries.

Upstream product

• 33208-47-8 4-O-benzyl-1,6:2,3-dianhydro-β-D-mannopyranose 

Downstream Products

• 1427042-94-1 1,3,6-tri-O-acetyl-4-O-benzyl-2-deoxy-2-fluoro-α-D-glucopyranose 
• 1427043-00-2 1,3,6-tri-O-acetyl-4-O-benzyl-2-deoxy-2-fluoro-β-D-glucopyranose 
• 97292-03-0 1,6-Anhydro-3,4-di-O-benzyl-2-deoxy-2-fluoro-β-D-glucopyranose 

Relevant academic research and scientific papers

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.

Stereoselective Synthesis of Fluorinated Galactopyranosides as Potential Molecular Probes for Galactophilic Proteins: Assessment of Monofluorogalactoside–LecA Interactions

The replacement of hydroxyl groups by fluorine atoms on hexopyranoside scaffolds may allow access to invaluable tools for studying various biochemical processes. As part of ongoing activities toward the preparation of fluorinated carbohydrates, a systematic investigation involving the synthesis and biological evaluation of a series of mono- and polyfluorinated galactopyranosides is described. Various monofluorogalactopyranosides, a trifluorinated, and a tetrafluorinated galactopyranoside have been prepared using a Chiron approach. Given the scarcity of these compounds in the literature, in addition to their synthesis, their biological profiles were evaluated. Firstly, the fluorinated compounds were investigated as antiproliferative agents using normal human and mouse cells in comparison with cancerous cells. Most of the fluorinated compounds showed no antiproliferative activity. Secondly, these carbohydrate probes were used as potential inhibitors of galactophilic lectins. The first transverse relaxation-optimized spectroscopy (TROSY) NMR experiments were performed on these interactions, examining chemical shift perturbations of the backbone resonances of LecA, a virulence factor from Pseudomonas aeruginosa. Moreover, taking advantage of the fluorine atom, the 19F NMR resonances of the monofluorogalactopyranosides were directly monitored in the presence and absence of LecA to assess ligand binding. Lastly, these results were corroborated with the binding potencies of the monofluorinated galactopyranoside derivatives by isothermal titration calorimetry experiments. Analogues with fluorine atoms at C-3 and C-4 showed weaker affinities with LecA as compared to those with the fluorine atom at C-2 or C-6. This research has focused on the chemical synthesis of “drug-like” low-molecular-weight inhibitors that circumvent drawbacks typically associated with natural oligosaccharides.

The synthesis of mono- and difluorinated 2,3-dideoxy-d-glucopyranoses

The synthesis of 2,3-dideoxy-2,3-difluoro-d-glucose and 2,3-dideoxy-3-fluoro-d-glucose is reported in, respectively, 5 and 6 steps from d-glucal, using a fluorination strategy.

Synthesis of a dual-purpose 2-deoxy-2-fluoro-glucopyranosyl building block

We demonstrate a straightforward route to 1,3,6-tri-O-acetyl-4-O-benzyl-2- deoxy-2-fluoro-D-glucopyranose through potassium hydrogen fluoride opening of a Cerny epoxide under microwave irradiation followed by acetolysis. The fluoroglucose building block was used as a key intermediate in the synthesis of 2,20-dideoxy-2,20-difluoromaltose. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications1 to view the free supplemental file. Copyright Taylor & Francis Group, LLC.