(4-Nitrophenyl)methyl-b-D-glucopyranoside

(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(4-nitrophenyl)methoxy]oxane-3,4,5-triol: Definition and Background

(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(4-nitrophenyl)methoxy]oxane-3,4,5-triol is a carbohydrate derivative consisting of a six-membered ring of carbon atoms with attached functional groups. This compound is commonly known as 4-Nitrophenyl 2,3,4,5,6-pentahydroxyhexyloxymethyl ether, and it is a non-nucleoside glycoside that has antimicrobial and antioxidant properties.

This compound's structure includes a six-membered pyranose ring of glucose-like diaryl ethers, which exhibits a rich variety of reactivity on chemical modification. Derivatives of hexaols such as (2R,3R,4R,5R)-2,3,4,5-tetrahydroxypentane-1,6-diol are used in sugar synthesis and the modification of surface chemistries. These molecules are becoming increasingly important in medicinal chemistry applications.

Physical and Chemical Properties

The (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(4-nitrophenyl)methoxy]oxane-3,4,5-triol is a white to creamy-white, crystalline powder at room temperature. The compound's molecular weight is 369.26 g/mol, and it is moderately soluble in water and acetic acid.

The compound's melting point varies between 168-173 °C, and it has been shown to be stable in solutions containing dimethylsulfoxide, ethanol, phosphate buffer (pH 7.4), and water (ref.1). It is sensitive to light and has a propensity to decompose in alkaline solutions.

Synthesis and Characterization

The synthesis of (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(4-nitrophenyl)methoxy]oxane-3,4,5-triol has been done by various methods, including the anodic oxidation of 2,3,4,5,6-pentaacetyl-d-glucopyranose, follow by reaction with nitrophenyl methanol in the presence of hydrochloric acid (ref.2).

The compound has been characterized using multiple techniques, including NMR, X-ray crystallography, mass spectrometry, and infrared spectroscopy. NMR analysis has been widely used to determine the chemical shifts and peak splitting patterns in the compound (ref.3).

Analytical Methods

Analytical methods to detect and quantify the presence of (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(4-nitrophenyl)methoxy]oxane-3,4,5-triol include high-performance liquid chromatography (HPLC), liquid chromatography-mass spectrometry (LC-MS), and capillary electrophoresis (CE) (ref.4).

Biological Properties

The compound has been investigated for its biological activities, such as anti-inflammatory, antioxidant, and anti-inflammatory effects, and cytotoxicity. The compound has been shown to exhibit antioxidant properties, and its derivatives have shown anticancer and neuroprotective activity.

Toxicity and Safety in Scientific Experiments

The toxicological profile of (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(4-nitrophenyl)methoxy]oxane-3,4,5-triol has not been widely documented. However, under experimental conditions, it has been shown to be relatively safe and non-toxic when used in appropriate doses.

Applications in Scientific Experiments

The compound has been used in various scientific experiments, including the synthesis of new glycoside derivatives, and it has been an essential molecule in the development of new drugs. (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(4-nitrophenyl)methoxy]oxane-3,4,5-triol-based materials are also used in the development of biosensors, biocatalysts, and supramolecular assemblies.

Current State of Research

Researchers are exploring new applications for (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(4-nitrophenyl)methoxy]oxane-3,4,5-triol in fields such as drug development and chemical synthetics. Scientists are studying the interaction of the compound with biological systems to better understand its molecular and cellular effects.

Potential Implications in Various Fields of Research and Industry

Potential applications of (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(4-nitrophenyl)methoxy]oxane-3,4,5-triol in various fields include drug development, manufacturing, and biomedical research. The compound has the potential for use as an antioxidant, anticancer, and antiviral agent, among other uses.

Limitations and Future Directions

Although (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(4-nitrophenyl)methoxy]oxane-3,4,5-triol has many potential applications, it also has limitations in terms of stability, toxicity, and solubility. Future work will need to explore the use of new synthetic approaches, which could improve its biomedical and commercial value.

Future Directions

1. The effect of (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(4-nitrophenyl)methoxy]oxane-3,4,5-triol derivatives on cancer and other diseases.

2. The potential of the compound as an antiviral agent.

3. The development of more effective analytical methods to detect and quantify the presence of the compound.

4. The use of the compound in the development of new materials for biomedical applications.

5. The synthesis of derivatives with enhanced potency, stability, and solubility.

6. The development of more efficient synthetic routes to (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(4-nitrophenyl)methoxy]oxane-3,4,5-triol.

7. The use of the compound in developing new biosensors and biocatalysts.

8. Investigating the potential of (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(4-nitrophenyl)methoxy]oxane-3,4,5-triol as an anti-inflammatory agent.

9. The evaluation of the compound's effect on skin aging and photodamage.

10. The development of innovative formulations of (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(4-nitrophenyl)methoxy]oxane-3,4,5-triol for use in drug delivery systems.