Methyl 4,6-O-benzylidene-a-D-glucopyranoside

甲基-4,6-O-苯亚甲基-α-D-吡喃葡萄糖苷，

Methyl 4,6-O-benzylidene-alpha-D-glucopyranoside (MBG) is a monosaccharide derivative that belongs to the class of benzylidene derivatives. It is commonly used in organic chemistry as a carbohydrate derivative that plays an essential role in the synthesis of various carbocyclic analogs. The compound was first synthesized in the 1960s and has since been used for different scientific applications such as lectin chromatography, antibody glycosylation, and drug development.

Synthesis and Characterization:

MBG can be synthesized through chemical transformation of glucose. The synthesis is achieved by the reaction of glucose with benzaldehyde in the presence of acid catalysts such as hydrochloric acid, sulfuric acid, and trifluoroacetic acid. The products obtained in the reaction are purified through recrystallization and characterized through various analytical methods.

Analytical Methods:

The most commonly used analytical methods for MBG are nuclear magnetic resonance (NMR), infrared spectroscopy (IR), and mass spectrometry (MS).

Biological Properties:

MBG has been found to have several biological properties. It shows promising results in the treatment of cancer cells, as it has been observed to inhibit the growth of several cancer cell types. It also has potent anti-inflammatory properties and has been proven effective in reducing inflammation in animal models.

Toxicity and Safety in Scientific Experiments:

Although MBG exhibits low cytotoxicity, it is essential to note that excess concentrations may result in adverse effects on biological systems. It is also important to conduct experiments in well-ventilated areas as the compound has been found to be irritant to the respiratory system.

Applications in Scientific Experiments:

MBG is a valuable reagent in chemical synthesis, lectin chromatography, and antibody glycosylation. It is also used in drug development and has shown positive results in combination therapy for the treatment of cancer.

Current State of Research:

The current state of research on MBG is focused on enhancing its biological and chemical properties to optimize its therapeutic potential. There is also ongoing research that focuses on developing more efficient synthesis pathways with higher yields.

Potential Implications in Various Fields of Research and Industry:

MBG has potential implications in various fields of research and industry such as cancer research, drug development, and carbohydrate chemistry. The compound is also useful in the development of glycomics research tools.

Limitations and Future Directions:

One of the main limitations of MBG is its synthetic route, which may cause side reactions resulting in low yields. Future research should focus on developing more efficient and environmentally friendly synthetic routes. Other future directions include the development of new derivatives with improved biological properties and the investigation of new applications in material science.

In conclusion, Methyl 4,6-O-benzylidene-alpha-D-glucopyranoside is a valuable carbohydrate derivative with promising properties and applications in various fields. Its unique properties and potential implications make it an interesting compound worth exploring further.

Product name: Methyl-4,6-O-benzylidene-a-D-glucopyranoside 

CAS: 3162-96-7             F.M.: C₁₄H₁₈O₆                            F.W.: 282.29

(a) The stationary phase is silica gel. The mobile phase is AcOEt. (b) The stationary phase is C₁₈ colum, the mobile phase is water-methol (V : V = 6 : 4) and the detecting wave length is 210nm.

References:

1. van Cleve JW, Carbohydr. Res. 1971, 17, p461-4