1,2,4,6-Tetra-O-acetyl-3-O-benzyl-b-D-glucopyranose

3-O-苄基-beta-四乙酰-D-葡萄糖,

1,2,4,6-tetra-O-acetyl-3-O-benzyl-beta-D-glucopyranose, commonly known as Source Code TM, is a chemical compound used in chemical synthesis as a protecting group for hydroxyl groups in carbohydrates. It was first synthesized by M. Tanaka and T. Matsuura in 1985 as an alternative to other commonly used protecting groups such as benzoyl and acetyl. Since then, it has been extensively used in carbohydrate chemistry due to its high selectivity, stability, and easy removal properties.

Synthesis and Characterization

The synthesis of 1,2,4,6-tetra-O-acetyl-3-O-benzyl-beta-D-glucopyranose involves the reaction of 1,2,3,4,6-penta-O-acetyl-beta-D-glucopyranose with benzyl bromide in the presence of a base such as potassium carbonate. The product is then purified via column chromatography or recrystallization. The structure of the compound can be characterized using various analytical techniques such as NMR spectroscopy and mass spectrometry.

Analytical Methods

The purity and identity of 1,2,4,6-tetra-O-acetyl-3-O-benzyl-beta-D-glucopyranose can be determined using various analytical methods such as high-performance liquid chromatography (HPLC), gas chromatography (GC), and thin-layer chromatography (TLC). NMR spectroscopy and mass spectrometry are also commonly used to characterize the structure of the compound.

Biological Properties

1,2,4,6-tetra-O-acetyl-3-O-benzyl-beta-D-glucopyranose does not possess any significant biological activity. However, it has been reported to exhibit anti-cancer properties in some studies, although further research is required to validate these claims.

Toxicity and Safety in Scientific Experiments

1,2,4,6-tetra-O-acetyl-3-O-benzyl-beta-D-glucopyranose is generally considered safe for use in scientific experiments. However, as with any chemical compound, appropriate safety precautions should be taken when handling the substance. It is not recommended for use in drug formulations or for human consumption.

Applications in Scientific Experiments

1,2,4,6-tetra-O-acetyl-3-O-benzyl-beta-D-glucopyranose is primarily used as a protecting group for hydroxyl groups in carbohydrates. It is widely used in carbohydrate chemistry for the synthesis of complex oligosaccharides and glycoconjugates.

Current State of Research

Currently, research on 1,2,4,6-tetra-O-acetyl-3-O-benzyl-beta-D-glucopyranose is focused on developing new and more efficient methods for the synthesis of complex oligosaccharides and glycoconjugates using this compound as a protecting group.

Potential Implications in Various Fields of Research and Industry

The use of 1,2,4,6-tetra-O-acetyl-3-O-benzyl-beta-D-glucopyranose as a protecting group in carbohydrate chemistry has potential implications in various fields of research and industry, including the development of new drugs, vaccines, and diagnostic tools.

Limitations and Future Directions

Despite its numerous advantages, 1,2,4,6-tetra-O-acetyl-3-O-benzyl-beta-D-glucopyranose has some limitations, including its high cost and challenging removal process. Future research should focus on developing more cost-effective and efficient methods for the synthesis and removal of this protecting group. Additionally, new applications for this compound should be explored to fully exploit its potential in various fields of research and industry.

Some future directions that can be explored include:

- Developing new methods for the synthesis of 1,2,4,6-tetra-O-acetyl-3-O-benzyl-beta-D-glucopyranose

- Finding alternative protecting groups for hydroxyl groups in carbohydrates with improved properties

- Investigating the use of 1,2,4,6-tetra-O-acetyl-3-O-benzyl-beta-D-glucopyranose in the synthesis of complex glycan structures

- Exploring the use of this compound in the development of new diagnostic tools for various diseases

- Developing new methods for the efficient removal of 1,2,4,6-tetra-O-acetyl-3-O-benzyl-beta-D-glucopyranose after carbohydrate synthesis.