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  • 53598-03-1 , 甲基-2,3-O-二苯甲酰基-4,6-O-苄叉-beta-D-吡喃半乳糖苷, CAS:53598-03-1
53598-03-1 , 甲基-2,3-O-二苯甲酰基-4,6-O-苄叉-beta-D-吡喃半乳糖苷, CAS:53598-03-1

53598-03-1 , 甲基-2,3-O-二苯甲酰基-4,6-O-苄叉-beta-D-吡喃半乳糖苷, CAS:53598-03-1

53598-03-1, Methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-b-D-galactopyranoside,
甲基-2,3-O-二苯甲酰基-4,6-O-苄叉-beta-D-吡喃半乳糖苷,
CAS:53598-03-1
C28H26O8 / 490.5
MFCD04039604

Methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-b-D-galactopyranoside

甲基-2,3-O-二苯甲酰基-4,6-O-苄叉-beta-D-吡喃半乳糖苷,

Methyl 2,3-dibenzoyl-4,6-O-benzylidene-beta-D-galactopyranoside (MDBBG) is a carbohydrate derivative that has garnered significant attention in recent years for its unique synthesis and properties. MDBBG is a member of the benzylidene galactoside family and has been researched extensively in various fields of science and industry, such as medicine, biochemistry, and materials science. This paper aims to provide an overview of the fundamental aspects of MDBBG, including its definition, properties, synthesis and characterization, analytical methods, biological properties, toxicity, and safety in scientific experiments, as well as its current state of research, potential implications in various fields of research and industry, limitations, and future directions.

Synthesis and Characterization:

MDBBG is synthesized via a multistep reaction involving galactose, benzaldehyde, benzoyl chloride, and benzylidene chloride. The starting material, galactose, undergoes a condensation reaction with benzaldehyde to form dibenzoyl galactose. This intermediate compound is then reacted with benzylidene chloride to form MDBBG. The resulting product is characterized by various spectroscopic techniques, such as ^1H and ^13C NMR, IR, and UV-visible spectroscopy.

Analytical Methods:

MDBBG can be analyzed using various techniques, such as high-performance liquid chromatography (HPLC), gas chromatography-mass spectrometry (GC-MS), and thin-layer chromatography (TLC). HPLC is a commonly used technique to separate and quantify MDBBG from its impurities. GC-MS is used for the identification and quantification of volatile components of MDBBG, while TLC is used for qualitative analysis.

Biological Properties:

MDBBG has been studied extensively for its biological properties, especially its anti-tumor and anti-inflammatory activities. The compound has shown promising results in inhibiting the growth of cancer cells by inducing apoptosis and inhibiting cell migration. It has also demonstrated anti-inflammatory activity by reducing the production of pro-inflammatory cytokines and chemokines.

Toxicity and Safety in Scientific Experiments:

MDBBG has been tested for its toxicity and safety in various scientific experiments. The compound has been found to be safe for use in vitro and in vivo at concentrations up to 100 μM. However, it is important to note that higher doses of MDBBG may cause cytotoxicity and cell death.

Applications in Scientific Experiments:

MDBBG has found numerous applications in scientific experiments, ranging from medicinal chemistry to materials science. The compound has been used as a starting material for the synthesis of various benzylidene galactosides and glycosides. It has also been used as a chiral auxiliary in the synthesis of various natural products.

Current State of Research:

MDBBG is an active area of research, with numerous studies exploring its properties and potential applications. Recent studies have focused on the development of new synthetic strategies for MDBBG and its derivatives. Additionally, research has been conducted on the biological activities of MDBBG and its potential use in drug discovery.

Potential Implications in Various Fields of Research and Industry:

MDBBG has potential implications in various fields of research and industry, including medicinal chemistry, materials science, and organic synthesis. Its anti-tumor and anti-inflammatory properties make it a promising candidate for the development of new anti-cancer drugs. In materials science, MDBBG has found applications as a chiral selector and as a component in the development of polymeric materials. In organic synthesis, MDBBG has been used as a chiral auxiliary in the asymmetric synthesis of various natural products.

Limitations and Future Directions:

Despite its potential, MDBBG has limitations in its use due to its solubility in water and the lack of studies on its pharmacokinetics. Further research on the synthesis of new derivatives of MDBBG and their biological activities is needed to elucidate their potential in drug discovery. Moreover, the development of new analytical techniques for the detection and analysis of MDBBG is needed to expand its applications in various fields.

Future directions include exploring the potential of MDBBG as a chiral auxiliary in the synthesis of new natural products, investigating its pharmacokinetics, and conducting clinical trials on its anti-cancer and anti-inflammatory properties. Additionally, the development of new materials and technologies using MDBBG and its derivatives is a promising area of research. Finally, the use of MDBBG as a selective inhibitor of glycoside hydrolases for the development of new glycan-based drugs is an exciting new field of research.

Conclusion:

MDBBG is a unique carbohydrate derivative that has been extensively studied for its physical, chemical, and biological properties. Its anti-tumor and anti-inflammatory properties make it a promising candidate for drug discovery, and its applications in materials science and organic synthesis make it a versatile compound in various fields of research and industry. While more research is needed to fully elucidate the potential of MDBBG, current advancements in synthetic strategies and analytical techniques suggest that it is a compound with a bright future.

CAS Number53598-03-1
Product NameMethyl 2,3-dibenzoyl-4,6-O-benzylidene-beta-D-galactopyranoside
IUPAC Name[(4aR,6R,7R,8S,8aS)-7-benzoyloxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] benzoate
Molecular FormulaC₂₈H₂₆O₈
Molecular Weight490.5
InChIInChI=1S/C28H26O8/c1-31-28-24(35-26(30)19-13-7-3-8-14-19)23(34-25(29)18-11-5-2-6-12-18)22-21(33-28)17-32-27(36-22)20-15-9-4-10-16-20/h2-16,21-24,27-28H,17H2,1H3/t21-,22+,23+,24-,27?,28-/m1/s1
SMILESCOC1C(C(C2C(O1)COC(O2)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)OC(=O)C5=CC=CC=C5
SynonymsMethyl 4,6-O-(Phenylmethylene)-β-D-galactopyranoside Dibenzoate;
CAS No: 53598-03-1 MDL No: MFCD04039604 Chemical Formula: C28H26O8 Molecular Weight: 490.5
References: 1. Hu G, Vasella A, Helv. Chim. Acta 2002, Vol85, Issue 12, p4369-4391

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