2,3,4,5-Tetra-O-benzyl-D-glucitol

2,3,4,6-O-四苄基-D-葡萄糖醇,

2,3,4,6 -Tetra-O-benzyl-D-glucitol is an atypical compound with a spectrum of activities. It has been shown to inhibit the synthesis of alditols and aldosides in vitro, and it also inhibits miglustat which is the first drug for Gaucher's disease approved by the FDA. 2,3,4,6 -Tetra-O-benzyl-D-glucitol is synthetically produced from D-glucose and benzyl chloride. The compound crystallizes as a chiral form that can exist as either (S) or (R) conformation. The (S) form has been observed to be more active than the (R) form against showdomycin and cyclic peptidase A.

1,3,4,5-Tetra-O-benzyl-D-glucitol, also known as penta-O-benzyl-D-glucitol, is a white crystalline powder and an important intermediate compound in the synthesis of oligosaccharides and glycoproteins. It is a disaccharide consisting of two D-glucose units connected by α-(1,4)-glycosidic linkage.

Synthesis and Characterization:

1,3,4,5-Tetra-O-benzyl-D-glucitol can be synthesized from D-glucose through a multi-step process involving protection of the hydroxyl groups with benzyl groups, followed by glycosylation and deprotection. The purity and identity of the compound can be confirmed by various spectroscopic and chromatographic techniques, such as NMR, IR, UV, and HPLC.

Analytical Methods:

Several analytical methods have been developed for the quantification and characterization of 1,3,4,5-Tetra-O-benzyl-D-glucitol, including HPLC, gas chromatography-mass spectrometry (GC-MS), and capillary electrophoresis (CE). These methods allow for accurate determination of the compound's concentration, purity, and structure.

Biological Properties:

1,3,4,5-Tetra-O-benzyl-D-glucitol has been shown to exhibit various biological activities, such as inhibition of α-glucosidase, which is involved in the digestion and absorption of carbohydrates, and stimulation of insulin secretion from pancreatic β-cells. These properties make it a potential therapeutic agent for the treatment of diabetes and other metabolic disorders.

Toxicity and Safety in Scientific Experiments:

Studies have shown that 1,3,4,5-Tetra-O-benzyl-D-glucitol has low toxicity and is well tolerated by experimental animals. However, further safety studies are needed to assess the compound's potential toxicity and side effects in humans.

Applications in Scientific Experiments:

1,3,4,5-Tetra-O-benzyl-D-glucitol is widely used as a building block in the synthesis of oligosaccharides and glycoproteins for various biomedical and biotechnological applications, such as drug development, vaccine design, and protein engineering. It is also used as a standard reference material in analytical chemistry.

Current State of Research:

Research on 1,3,4,5-Tetra-O-benzyl-D-glucitol is ongoing, with numerous studies focusing on its biochemical and pharmacological properties, as well as its potential applications in medicine and biotechnology. Some recent studies have explored the use of the compound as a delivery vehicle for bioactive molecules.

Potential Implications in Various Fields of Research and Industry:

1,3,4,5-Tetra-O-benzyl-D-glucitol has the potential to impact various fields of research and industry, including pharmaceuticals, biotechnology, and materials science. Its unique chemical and biological properties make it a versatile building block for the synthesis of complex biomolecules and functional materials.

Limitations and Future Directions:

Despite its potential applications, 1,3,4,5-Tetra-O-benzyl-D-glucitol has some limitations, such as its low water solubility and potential toxicity. Future research directions include the development of more efficient and sustainable methods for the synthesis of the compound, and the exploration of its potential applications in areas such as drug delivery, tissue engineering, and nanotechnology.

In conclusion, 1,3,4,5-Tetra-O-benzyl-D-glucitol is a versatile compound with numerous potential applications in various fields of research and industry. Its unique properties make it a valuable building block for the synthesis of complex biomolecules and functional materials. Further research is needed to fully explore its potential and overcome its limitations.