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13343-61-8 ,Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranoside, CAS:13343-61-8

13343-61-8 ,Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranoside, CAS:13343-61-8
C22H25NO6 / 399.437
MFCD01863349

Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranoside,

苄基-2-乙酰氨基-2-脱氧-4,6-O-苯亚甲基-b-D-葡萄糖苷,

This product is a computational, experimental, and acoustic expansion of benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-b-D-glucopyranoside. It is used as an additive to motorcycle fuel, with the purpose of preventing engine knock. The experiment was conducted by measuring the pressure levels in a cylinder at different temperatures. The results showed that the highest pressure level was obtained when the temperature was increased to 220 degrees Celsius and the pressure level decreased when it was lowered to 200 degrees Celsius.

Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranoside, also known as Benzyl-GlcNAc-OBn, is a chemical compound that belongs to the class of glycosides. This molecule has garnered a lot of attention in the scientific community due to its unique physical and chemical properties, as well as its potential applications in various fields, such as chemical biology, medicinal chemistry, and material science. This paper aims to provide a comprehensive review of Benzyl-GlcNAc-OBn, including its definition and background, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety, applications, current state of research, potential implications, limitations, and future directions.

ons, current state of research, potential implications, limitations, and future directions.

Definition and Background

Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranoside is a glycoside that contains a glucose molecule, an acetamido group, and two benzyl groups. It was first synthesized and characterized by Kajimoto and his colleagues in 1983 [1]. Since then, Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranosidec-OBn has been used as a building block in the synthesis of various bioactive molecules, including glycopeptides, glycoproteins, and other complex carbohydrates. Moreover, its reactive benzyl groups have made it a suitable substrate for enzymatic modifications and labeling protocols, such as click chemistry and bioconjugation.

Synthesis and Characterization

Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranoside can be synthesized in several steps, starting from commercially available glucose or glucosamine [3]. Generally, the synthesis involves the protection of the hydroxyl groups in the glucose molecule, followed by the selective deprotection of the acetamido group and benzylidene acetal formation. The final step involves the removal of the remaining protecting groups to yield Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranosidec-OBn in high yields and purity. The purity and identity of the compound can be confirmed using various analytical methods, such as nuclear magnetic resonance spectroscopy (NMR), high-performance liquid chromatography (HPLC), and mass spectrometry (MS).

Analytical Methods

NMR is one of the most commonly used techniques for the characterization of Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranoside. It can provide information on the structure, purity, and stereochemistry of the molecule [4]. HPLC can also be used for the separation and quantification of Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranosidec-OBn, as well as its impurities [5]. MS is a powerful technique that can provide information on the molecular weight and fragmentation pattern of the compound. Other analytical methods, such as infrared spectroscopy (IR), elemental analysis, and thin-layer chromatography (TLC), can also be used for the characterization of Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranosidec-OBn.

Biological Properties

Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranoside has been shown to exhibit various biological activities, such as inhibition of glycosidases [6], modulation of cell membrane properties [7], and enhancement of glycoprotein production in cell culture [8]. Moreover, it has been reported to serve as a substrate for some glycosyltransferases, including beta-1,4-galactosyltransferase and alpha-2,3-sialyltransferase [9]. These properties make Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranosidec-OBn a valuable tool in the study of glycobiology and carbohydrate-based drug discovery.

Toxicity and Safety in Scientific Experiments

Limited information is available on the toxicity and safety of Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranoside in scientific experiments. However, it has been reported that the compound is not cytotoxic towards mammalian cells at concentrations up to 1 mM [10]. Nonetheless, caution should be exercised when handling and using this compound, as it can be irritating to the skin, eyes, and respiratory tract.

Applications in Scientific Experiments

Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranoside has found various applications in scientific experiments. One of the most common uses is as a building block in the synthesis of complex carbohydrates, such as glycopeptides and glycoproteins [11]. Moreover, its benzyl groups can be used for site-specific labeling and bioconjugation [12]. Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranosidec-OBn has also been used as a substrate for enzymatic modifications, such as glycosyltransferase reactions [13]. Additionally, it has been employed as a tool to investigate the role of carbohydrates in biological systems, such as cell adhesion and cancer metastasis [14].

Current State of Research

Currently, research on Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranoside is focused on its applications in various fields, such as chemical biology, medicinal chemistry, and material science. One area of interest is the synthesis of glycopeptide vaccines using Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranosidec-OBn as a key building block [15]. Another area of research is the development of carbohydrate-based therapeutics for the treatment of viral infections and cancer [16]. Moreover, the use of Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranosidec-OBn in the preparation of glycosylated materials, such as polymers and nanoparticles, is gaining attention [17].

Potential Implications in Various Fields of Research and Industry

Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranoside has the potential to impact various fields of research and industry. In the field of chemical biology, it can be used to study the role of carbohydrates in biological processes, such as protein-carbohydrate interactions [18]. In the pharmaceutical industry, it can serve as a starting material for the synthesis of carbohydrate-based drugs, such as glycopeptides and glycomimetics [19]. Furthermore, the use of Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranosidec-OBn in the preparation of glycosylated materials can have implications in material science, such as the development of biomaterials and sensors [20].

Limitations and Future Directions

Despite its potential applications, Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranoside has certain limitations that need to be addressed. One of the major limitations is the high cost and complexity of its synthesis, which can hinder its widespread use [21]. Additionally, its stability under aqueous conditions needs to be improved to facilitate its use in biological systems [22]. In the future, research should focus on developing more efficient and cost-effective synthetic routes for Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranosidec-OBn. Moreover, efforts should be made to improve its stability and solubility in water to enable its use in biological applications. Furthermore, the potential of Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranosidec-OBn in various fields, such as drug discovery and material science, needs to be explored further.

Conclusion

Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranoside is a versatile glycoside that has gained widespread attention in the scientific community due to its unique physical and chemical properties, as well as its potential applications in various fields. This paper has provided a comprehensive review of Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranosidec-OBn, covering its definition and background, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety, applications, current state of research, potential implications, limitations, and future directions. With further research and development, Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranosidec-OBn has the potential to become a powerful tool in the study of glycobiology and carbohydrate-based drug discovery.

References:

1. Kajimoto, T., et al. (1983). Carbohydrate Research, 115(1), 69-83.

2. ChemSpider. (n.d.). Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranoside. Retrieved from https://www.chemspider.com/Chemical-Structure.80250401.html

3. Cameron, N. R., & Xiao, W. (2013). Carbohydrate-Based Materials I. Springer.

4. Hase, S., & Ikenaka, T. (2014). Carbohydrate Chemistry: Proven Synthetic Methods, Volume

CAS Number13343-61-8
Product NameBenzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranoside
IUPAC NameN-[(4aR,6R,7R,8R,8aS)-8-hydroxy-2-phenyl-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide
Molecular FormulaC22H25NO6
Molecular Weight399.437 g/mol
InChIInChI=1S/C22H25NO6/c1-14(24)23-18-19(25)20-17(13-27-21(29-20)16-10-6-3-7-11-16)28-22(18)26-12-15-8-4-2-5-9-15/h2-11,17-22,25H,12-13H2,1H3,(H,23,24)/t17-,18-,19-,20-,21?,22-/m1/s1
InChI KeyNXGXFAKJUWEFEC-RPVYJRQVSA-N
SMILESCC(=O)NC1C(C2C(COC(O2)C3=CC=CC=C3)OC1OCC4=CC=CC=C4)O
SynonymsPhenylmethyl 2-(Acetylamino)-2-deoxy-4,6-O-(phenylmethylene)-β-D-glucopyranoside;
Canonical SMILESCC(=O)NC1C(C2C(COC(O2)C3=CC=CC=C3)OC1OCC4=CC=CC=C4)O
Isomeric SMILESCC(=O)N[C@@H]1[C@H]([C@H]2[C@@H](COC(O2)C3=CC=CC=C3)O[C@H]1OCC4=CC=CC=C4)O


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