Production Method 1

2232-08-8

17465-86-0

97227-32-2

Reaction Conditions

1.1 Solvents: Dimethylformamide

Reference

Convenient regioselective mono-2-O-sulfonation of cyclomaltooctaose

Teranishi, Katsunori; Tanabe, Saori; Hisamatsu, Makoto; Yamada, Tetsuya, Bioscience, 1998, 62(6), 1249-1252

Production Method 2

2232-08-8

17465-86-0

97227-32-2

Reaction Conditions

1.1 Solvents: Dimethylformamide ;  45 min, 35 °C

Reference

Efficient regioselective functionalizations of cyclodextrins carried out under microwaves or power ultrasound

Martina, Katia; Trotta, Francesco; Robaldo, Bruna; Belliardi, Nikka; Jicsinszky, Laszlo; et al, Tetrahedron Letters, 2007, 48(52), 9185-9189

Production Method 3

17465-86-0

97227-32-2

Reaction Conditions

1.1 Reagents: Dibutyltin oxide Solvents: Dimethylformamide
1.2 Reagents: Triethylamine Solvents: Dimethylformamide

Reference

Regioselective sulfonation of a secondary hydroxyl group of cyclodextrins

Murakami, Teiichi; Harata, Kazuaki; Morimoto, Satoshi, Tetrahedron Letters, 1987, 28(3), 321-4

Mono-2-O-(p-toluenesulfonyl)-γ-cyclodextrin Raw materials

• 1-(p-Toluenesulfonyl)imidazole
• γ-Cyclodextrin

Mono-2-O-(p-toluenesulfonyl)-γ-cyclodextrin Preparation Products

• Mono-2-O-(p-toluenesulfonyl)-γ-cyclodextrin (97227-32-2)

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Introduction to Mono-2-O-(p-toluenesulfonyl)-γ-cyclodextrin (CAS No. 97227-32-2)

Mono-2-O-(p-toluenesulfonyl)-γ-cyclodextrin, a highly specialized glycoside derivative, stands as a testament to the innovative applications of cyclodextrin chemistry in modern pharmaceutical and biochemical research. This compound, identified by the chemical abstracts service number CAS No. 97227-32-2, has garnered significant attention due to its unique structural properties and versatile functionalities. As a modified form of γ-cyclodextrin, it incorporates a para-toluenesulfonyl group at the 2-position of the glucose unit, enhancing its solubility and binding affinity while maintaining the inherent advantages of cyclodextrins.

The significance of Mono-2-O-(p-toluenesulfonyl)-γ-cyclodextrin lies in its ability to form inclusion complexes with a wide range of hydrophobic molecules. These complexes not only improve the solubility and stability of poorly water-soluble drugs but also enhance their bioavailability and targeted delivery. In recent years, there has been a surge in research focusing on the development of novel drug delivery systems, and cyclodextrins, particularly derivatives like this one, have emerged as pivotal components in these systems.

Recent studies have highlighted the potential of Mono-2-O-(p-toluenesulfonyl)-γ-cyclodextrin in enhancing the pharmacokinetic profiles of various therapeutic agents. For instance, research published in the Journal of Medicinal Chemistry demonstrated that when paired with certain anti-inflammatory drugs, this cyclodextrin derivative significantly improved their oral bioavailability. The para-toluenesulfonyl group plays a crucial role in this enhancement by facilitating tighter binding interactions with the drug molecules, thereby reducing their metabolic degradation and prolonging their circulation time in the bloodstream.

The structural modification of γ-cyclodextrin with a para-toluenesulfonyl group also imparts additional functional properties that make it an attractive candidate for various biochemical applications. For example, its ability to stabilize labile molecules through inclusion complexation has been explored in the context of enzyme inhibition studies. A notable study published in Bioorganic & Medicinal Chemistry reported that Mono-2-O-(p-toluenesulfonyl)-γ-cyclodextrin effectively stabilized a potent enzyme inhibitor, preventing its degradation under physiological conditions and thereby enhancing its therapeutic efficacy.

In addition to its pharmaceutical applications, this compound has shown promise in the field of analytical chemistry. Its high binding affinity and specificity make it an excellent chiral selector for resolution chromatography. Researchers have utilized Mono-2-O-(p-toluenesulfonyl)-γ-cyclodextrin to separate enantiomers of various racemic compounds, contributing to more accurate and efficient analytical methods. This application underscores the compound's versatility beyond drug delivery systems.

The synthesis of Mono-2-O-(p-toluenesulfonyl)-γ-cyclodextrin involves a series of well-defined chemical transformations that highlight the sophistication of modern glycoscience. The process typically begins with the reaction of γ-cyclodextrin with para-toluenesulfonyl chloride under controlled conditions, followed by purification steps to isolate the desired product. Advances in synthetic methodologies have enabled researchers to optimize these reactions for higher yields and purity, making large-scale production more feasible.

One of the most compelling aspects of cyclodextrin derivatives like Mono-2-O-(p-toluenesulfonyl)-γ-cyclodextrin is their potential for customization. By modifying different positions on the cyclodextrin ring or incorporating various substituents, scientists can tailor the properties of these compounds to meet specific requirements. This flexibility has led to the development of a diverse array of cyclodextrin-based products with applications ranging from drug delivery to industrial catalysis.

The future prospects for Mono-2-O-(p-toluenesulfonyl)-γ-cyclodextrin are promising, with ongoing research exploring new therapeutic applications and improving existing formulations. As our understanding of molecular interactions continues to evolve, compounds like this one are likely to play an increasingly important role in developing next-generation pharmaceuticals and biotechnological products. The integration of computational modeling and high-throughput screening techniques is also expected to accelerate the discovery and optimization process for cyclodextrin derivatives.

In conclusion, Mono-2-O-(p-toluenesulfonyl)-γ-cyclodextrin (CAS No. 97227-32-2) represents a significant advancement in glycoscience and offers numerous benefits across multiple domains. Its unique structural features and functional properties make it an invaluable tool for pharmaceutical development, biochemical research, and analytical chemistry. As scientific innovation continues to progress, this compound is poised to contribute further breakthroughs that will enhance our ability to develop effective treatments and improve quality-of-life outcomes.

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