1,2-O-Isopropylidene-5-O-p-toluenesulfonyl-a-D-xylofuranose

5-O-对甲基苯磺酰基-1,2-O-异丙叉-D-木糖,

1,2-Isopropylidene-5-O-tosyl-D-xylofuranose is a stereochemically-defined carbohydrate molecule that belongs to the class of xylosides. It is a crystalline compound with white to off-white color, commonly used as a substrate for glycosylation reactions. The compound features a furanose ring with a tosylated xylopyranose unit attached to it. The tosyl group in the molecule is a protecting group for the hydroxyl group present in the carbohydrate.

Synthesis and Characterization:

There are various methods to synthesize 1,2-Isopropylidene-5-O-tosyl-D-xylofuranose, and they involve the protection of xylose using tosyl groups and the formation of a furanose ring. The most commonly used method involves the reaction of xylose with a mixture of p-toluenesulfonic acid and isopropylidene acetal. This reaction yields a mixture of isomers that can be separated using chromatography techniques.

Characterization of the compound is primarily done using NMR techniques, which can provide information about the stereochemistry and purity of the product. Other techniques such as IR spectroscopy, mass spectrometry, and X-ray crystallography can also be employed for characterization.

Analytical Methods:

High-performance liquid chromatography (HPLC) is a commonly used analytical method to separate and quantify 1,2-Isopropylidene-5-O-tosyl-D-xylofuranose from other compounds in a mixture. NMR spectroscopy can also be used to quantify the purity of the compound.

Biological Properties:

1,2-Isopropylidene-5-O-tosyl-D-xylofuranose is a non-nutritive carbohydrate and does not have any significant biological activity in human or animal systems. However, it can act as a substrate for enzymes such as glycosidases and glycosyltransferases in various biological processes.

Toxicity and Safety in Scientific Experiments:

There are no reported toxic effects of 1,2-Isopropylidene-5-O-tosyl-D-xylofuranose in scientific experiments. However, it is always recommended to handle the compound with care and follow standard laboratory safety procedures.

Applications in Scientific Experiments:

1,2-Isopropylidene-5-O-tosyl-D-xylofuranose is commonly used as a substrate for glycosylation reactions in synthetic organic chemistry. The compound is also used in the preparation of carbohydrate-based materials such as dendrimers, glycopeptides, and glycolipids.

Current State of Research:

The use of 1,2-Isopropylidene-5-O-tosyl-D-xylofuranose as a substrate for glycosylation reactions has been extensively studied, and various modifications to the molecule have been reported to improve its reactivity and selectivity. Recent research has also focused on the preparation of carbohydrate-based materials using this compound, and their potential applications in drug delivery and biomaterials.

Potential Implications in Various Fields of Research and Industry:

The use of 1,2-Isopropylidene-5-O-tosyl-D-xylofuranose in synthetic organic chemistry has various implications in the field of chemical synthesis, particularly in the synthesis of complex carbohydrate derivatives. The preparation of carbohydrate-based materials using this compound has potential applications in drug delivery, diagnostics, and tissue engineering.

Limitations and Future Directions:

One of the major limitations of 1,2-Isopropylidene-5-O-tosyl-D-xylofuranose is its low solubility at higher temperatures, which limits its use in some applications. Future research can focus on the development of new derivatives of the compound that have improved solubility and reactivity. Another direction for future research is to explore the potential applications of carbohydrate-based materials prepared using this compound in various biomedical fields such as regenerative medicine and drug delivery.