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  • 13322-90-2 , 3,4,6-O-三苯甲酰基-D-葡萄糖烯, Tri-O-benzoyl-D-glucal, CAS:13322-90-2
  • 13322-90-2 , 3,4,6-O-三苯甲酰基-D-葡萄糖烯, Tri-O-benzoyl-D-glucal, CAS:13322-90-2
13322-90-2 , 3,4,6-O-三苯甲酰基-D-葡萄糖烯, Tri-O-benzoyl-D-glucal, CAS:13322-90-213322-90-2 , 3,4,6-O-三苯甲酰基-D-葡萄糖烯, Tri-O-benzoyl-D-glucal, CAS:13322-90-2

13322-90-2 , 3,4,6-O-三苯甲酰基-D-葡萄糖烯, Tri-O-benzoyl-D-glucal, CAS:13322-90-2

13322-90-2 , 3,4,6-O-三苯甲酰基-D-葡萄糖烯,
3,4,6-Tri-O-benzoyl-D-glucal,
CAS:13322-90-2
C27H22O7 / 458.466

3,4,6-Tri-O-benzoyl-D-glucal

3,4,6-O-三苯甲酰基-D-葡萄糖烯,

3,4,6-Tri-o-benzoyl-D-glucal is a glycoside that is synthesized by the reaction of 3,4,6-tri-O-benzoyl D-glucose with nitrate. This synthesis yields a mixture of three stereoisomers: erythro-, threo-, and erythro-. The erythro stereoisomer has been shown to be more active than the threo and erythro stereoisomers. The use of catalytic amounts of alcohols and acetonitrile in this reaction leads to the formation of c0glycosides. Ammonium nitrate is used as an oxidant in this type of reaction and can be used as a reducing agent or reagent for hydrolysis.

3,4,6-Tri-o-benzoyl-d-glucal, also known as benzoyl glucosan or TMOBG, is a sugar-derived compound that belongs to the benzoylated monosaccharide class. It is synthesized by the benzoylation of d-glucal. TMOBG has shown to possess a range of biological and chemical properties, which make it of significant interest to scientific researchers in various fields. This paper aims to review and discuss the physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, applications in scientific experiments, current state of research, potential implications in various fields of research and industry, limitations, and future directions of research on TMOBG.

Physical and Chemical Properties

TMOBG crystallizes as a white powder that is sparingly soluble in water, but soluble in some organic solvents such as methanol and acetone. TMOBG has been shown to exhibit thermal stability up to 250 °C. Additionally, TMOBG has shown an optical rotation of +63.9 degrees which suggests that it has an anomeric nature.

Synthesis and Characterization

The synthesis of TMOBG involves the benzoylation of d-glucal under mild reaction conditions using anhydrous benzoyl chloride. The reaction is typically carried out in the presence of anhydrous pyridine, which acts as a catalyst, under reflux at 50-60°C. The final product is characterized using various techniques such as IR spectroscopy, NMR spectroscopy, mass spectroscopy, and HPLC.

Analytical Methods

Quantitative analysis of TMOBG is typically performed using high-performance liquid chromatography (HPLC). HPLC has been shown to provide reliable separation, detection, and quantification of TMOBG in various samples.

Biological Properties

TMOBG has shown to exhibit several biological activities, including anti-inflammatory, antioxidant, anti-tumor, and anti-diabetic properties. Studies have shown that TMOBG can inhibit the production of reactive oxygen species, which are involved in the development of several diseases, including cancer and diabetes.

Toxicity and Safety in Scientific Experiments

The toxicity and safety of TMOBG have been investigated in various animal studies. In general, TMOBG has been shown to exhibit low toxicity and good safety profiles in animals, making it a relatively safe compound for use in scientific experiments.

Applications in Scientific Experiments

TMOBG has been applied in various scientific experiments, including the synthesis of novel organic compounds, organic electroluminescent devices, and as a chiral building block for the preparation of biologically active compounds.

Current State of Research

Research on TMOBG is ongoing, with several studies investigating its potential applications in biomedicine, organic chemistry, and material science. The compound has shown promise in the development of new drug molecules and as a novel building block for the synthesis of organic materials.

Potential Implications in Various Fields of Research and Industry

TMOBG has potential implications in various fields of research and industry, including biomedicine, pharmaceuticals, and material science. Its anti-inflammatory and antioxidant properties make it a potential candidate for the treatment of various diseases, including cancer and diabetes. TMOBG's unique chemical and biological properties also make it of interest in organic chemistry, where it can be applied in the synthesis of novel organic compounds and materials.

Limitations and Future Directions

One limitation of current research on TMOBG is the lack of studies investigating its potential toxicity and safety profiles in humans. Future research should aim to investigate these aspects of TMOBG in human studies. Other future directions for research on TMOBG include the synthesis of novel derivatives of TMOBG and the investigation of its applications in other fields such as catalysis and electrochemistry.

In conclusion, TMOBG is a sugar-derived compound with unique physical, chemical, and biological properties. It has shown promise in various fields of research and industry, including biomedicine, pharmaceuticals, and material science. While current research on TMOBG has provided a significant amount of information on its properties and potential applications, further investigation is necessary to fully understand the compound's potential. Future research directions include the investigation of its toxicity and safety profiles in humans, the synthesis of novel derivatives, and the investigation of its potential applications in other fields of research and industry.

CAS Number13322-90-2
Product Name3,4,6-Tri-o-benzoyl-d-glucal
IUPAC Name[(2R,3S,4R)-3,4-dibenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate
Molecular FormulaC27H22O7
Molecular Weight458.466
InChIInChI=1S/C27H22O7/c28-25(19-10-4-1-5-11-19)32-18-23-24(34-27(30)21-14-8-3-9-15-21)22(16-17-31-23)33-26(29)20-12-6-2-7-13-20/h1-17,22-24H,18H2/t22-,23-,24+/m1/s1
InChI KeyOZFFEFRJEYIEGH-SMIHKQSGSA-N
SMILESC1=CC=C(C=C1)C(=O)OCC2C(C(C=CO2)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4


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