112233-64-4

Basic information

• Product Name: .beta.-D-Glucopyranose, 1,6-anhydro-3-deoxy-3-fluoro-4-O-(phenylmethyl)-
• Synonyms: .beta.-D-Glucopyranose, 1,6-anhydro-3-deoxy-3-fluoro-4-O-(phenylmethyl)-
• CAS NO: 112233-64-4
• Molecular Formula: C₁₃H₁₅FO₄
• Molecular Weight: 254.25
• Mol File: 112233-64-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 396.5±42.0 °C(Predicted)
• Appearance: /
• Density: 1.32±0.1 g/cm3(Predicted)
• PKA: 13.30±0.60(Predicted)
• CAS DataBase Reference: .beta.-D-Glucopyranose, 1,6-anhydro-3-deoxy-3-fluoro-4-O-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: .beta.-D-Glucopyranose, 1,6-anhydro-3-deoxy-3-fluoro-4-O-(phenylmethyl)-(112233-64-4)
• EPA Substance Registry System: .beta.-D-Glucopyranose, 1,6-anhydro-3-deoxy-3-fluoro-4-O-(phenylmethyl)-(112233-64-4)

Safety Data

• Hazardous Substances Data: 112233-64-4(Hazardous Substances Data)

Usage

Description

.beta.-D-Glucopyranose, 1,6-anhydro-3-deoxy-3-fluoro-4-O-(phenylmethyl)is a synthetic derivative of glucose, a natural sugar molecule, which has been modified by the addition of a fluoro and phenylmethyl group. This rare sugar molecule has potential applications in the pharmaceutical industry and as a chemical building block for the synthesis of other compounds. The structural modification of the glucose molecule may provide specific biological activities or properties that are not present in natural glucose, making it a subject of interest for research and development in the fields of medicinal chemistry and organic synthesis.

Uses

Used in Pharmaceutical Industry:
.beta.-D-Glucopyranose, 1,6-anhydro-3-deoxy-3-fluoro-4-O-(phenylmethyl)is used as a pharmaceutical compound for its potential biological activities and properties. The modification of the glucose molecule may impart specific characteristics that can be exploited for the development of new drugs or therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, .beta.-D-Glucopyranose, 1,6-anhydro-3-deoxy-3-fluoro-4-O-(phenylmethyl)is used as a chemical building block for the synthesis of other complex compounds. The unique structure of this modified sugar molecule can be utilized to create novel molecules with specific functions or properties, contributing to the advancement of chemical research and development.
Used in Medicinal Chemistry Research:
.beta.-D-Glucopyranose, 1,6-anhydro-3-deoxy-3-fluoro-4-O-(phenylmethyl)is also used in medicinal chemistry research to explore its potential as a therapeutic agent or as a component in the development of new drugs. .beta.-D-Glucopyranose, 1,6-anhydro-3-deoxy-3-fluoro-4-O-(phenylmethyl)-'s structure and properties make it an interesting candidate for further investigation and potential applications in the treatment of various diseases or conditions.

Upstream product

• 26540-44-3 4-O-benzyl-1,6:2,3-dianhydro-β-D-allopyranoside 
• 26540-43-2 1,6-anhydro-4-O-benzyl-3-O-methanesulfonyl-2-O-(4-toluenesulfonyl)-β-D-glucopyranose 

Relevant articles and documents

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.

SYNTHESES OF 3-DEOXY-3-SUBSTITUTED-D-GLUCOSE DERIVATIVES. PART I. IMPROVEMENTS IN PREPARATION OF AND NUCLEOPHILIC ADDITIONS TO 1,6:2,3-DIANHYDRO-4-O-BENZYL-Β-D-ALLOPYRANOSE

The yield of the five-step preparation of 1,6:2,3-dianhydro-4-O-benzyl-β-D-glucopyranose from 1,6-anhydro-β-D-glucopyranose has been raised to 33percent from 12percent by modifying conditions or methods for four of the steps.It has been demonstrated that