三氧苄基-D-葡萄糖烯, Tri-O-benzyl-D-glucal

3,4,6-Tri-O-benzyl-D-glucal is a benzyl protected, 2,3 unsaturated glucal used as a chiral intermediate. The C2-C3 double bond of the pyranose ring can be modified via a variety of reactions including: hydrogenation, oxidation, hydroxylation, and aminohydroxylation, to generate structural complexity. 3,4,6-Tri-O-benzyl-D-glucal also minimizes tedious protecting-group strategies required for fully oxygenated sugars. The products of 2,3 unsaturated glycosides as chiral intermediates have played a role in the synthesis of many biologically active compounds, such as, nucleosides and modified sugar derivatives.

Tri-O-benzyl-D-glucal (TBG) is a carbohydrate derivative with potential applications in various fields of research and industry, from organic synthesis to pharmaceuticals. In this paper, we provide an overview of the properties, synthesis, analytical methods, biological properties, toxicity, safety, and applications of TBG, as well as a summary of the current state of research and future directions.

Definition and Background

TBG is a protected form of glucal, a carbohydrate that has a cyclic hemiacetal structure and properties similar to glucose. In TBG, the three hydroxyl groups of the glucal are protected by benzyl groups, which can be selectively removed under specific conditions to produce various derivatives of TBG. TBG is widely used as a starting material for the synthesis of glycosides, glycopeptides, and other biologically active compounds.

Synthesis and Characterization

TBG can be synthesized in several ways, including the reaction of glucal with benzyl chloride under basic conditions or by benzylating the glucal with benzyl chloride in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) as a catalyst. TBG can be characterized using various techniques such as NMR, IR, and mass spectrometry.

Analytical Methods

TBG can be analyzed using various analytical methods, including high-performance liquid chromatography (HPLC), thin-layer chromatography (TLC), and nuclear magnetic resonance (NMR) spectroscopy.

Biological Properties

TBG exhibits various biological activities, including antibacterial, antifungal, and antiviral properties. TBG is also used as a chiral building block in the synthesis of various pharmaceuticals and natural products.

Toxicity and Safety in Scientific Experiments

The toxicity and safety of TBG have been evaluated in various scientific experiments. TBG has low toxicity and is considered safe to handle and use, with no significant side effects reported.

Applications in Scientific Experiments

TBG has a wide range of applications in scientific experiments, including in the synthesis of glycosides, glycopeptides, and other biologically active compounds. TBG is also used as a chiral building block in organic synthesis and in the preparation of carbohydrate-enzyme conjugates.

Current State of Research

Research on TBG is ongoing, with new applications and derivatives being developed. Recent studies have focused on the synthesis of new glycosides and derivatives of TBG, as well as the development of TBG-based drugs and biomaterials.

Potential Implications in Various Fields of Research and Industry

TBG has potential implications in various fields of research and industry, including organic synthesis, pharmaceuticals, and materials science. TBG-based compounds have potential applications as antimicrobials, anticancer agents, and drug delivery systems.

Limitations and Future Directions

Despite its potential, TBG has certain limitations, including its low solubility in water and its limited availability in large quantities. Future research directions include the development of new TBG derivatives with improved solubility and stability, as well as the development of new methods for the synthesis of TBG derivatives. Other future directions include the study of the biological properties of TBG derivatives and their potential applications in drug development and materials science.

Conclusion

In conclusion, TBG is a carbohydrate derivative with a wide range of potential applications in various fields of research and industry. This paper provides an overview of the properties, synthesis, analytical methods, biological properties, toxicity, safety, and applications of TBG, as well as a summary of the current state of research and future directions. TBG-based compounds have significant potential as new drugs and materials, and further research is needed to explore their full potential.

Product name: 3, 4, 6-Tri-O-benzyl-D-glucal     

CAS: 55628-54-1         M.F.: C₂₇H₂₈O₄        M.W._: 416.51

References:

1. Bolitt V, Mioskowski C, Lee SG, Falck JR, J. Org. Chem. 1990, Vol55, p5812-5813