80887-27-0 ,2-Acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-b-D-glucopyranosyl azide,
2-乙酰氨基-3-O-苄基-4,6-O-苯亚甲基-2-脱氧-b-D-吡喃葡萄糖基叠氮
CAS:80887-27-0
C22H24N4O5 / 424.46
MFCD23104224
2-乙酰氨基-3-O-苄基-4,6-O-苯亚甲基-2-脱氧-b-D-吡喃葡萄糖基叠氮,
2-Acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranosyl Azide: Definition and Background
2-Acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranosyl Azide (abbreviated as NABG) is a complex chemical compound classified as a glycoside. It is a synthetic carbohydrate derived from D-glucose and consists of a beta-linked glucopyranoside unit to which are attached protective benzyl and acetamido groups. Azide is added to the molecule to increase its reactivity in organic synthesis.
The synthesis of NABG was first reported by the researchers Pohlmann and Ley in 1985. Since then, several improvements have been made in the synthesis route, and NABG has become a widely used compound in organic synthesis, and research fields including nanotechnology, materials science, and drug development.
Synthesis and Characterization of NABG
The synthesis of NABG involves the use of several chemical reactions that requires careful optimization to obtain high yield and purity. One of the most common procedures used in the synthesis of NABG involves the esterification of benzyl alcohol with the hydroxyl group of the corresponding 2,3,4,6-tetra-O-acetyl-D-glucose. Acid-catalyzed benzylidene ring formation subsequently follows. After benzyl deprotection and sodium azide treatment, the final product, NABG, is obtained.
Different characterization methods, including nuclear magnetic resonance spectroscopy (NMR) and mass spectrometry, are used to confirm the identity and purity of NABG. NMR analysis of the product can confirm the presence of protective groups, while mass spectrometry confirms the molecular weight of the compound.
Analytical Methods for NABG
With the increasing use of NABG in a wide range of scientific research fields, the need for reliable and precise analytical methods for its detection and quantification is currently on the rise. Several analytical techniques have emerged, including high-performance liquid chromatography (HPLC), capillary electrophoresis (CE) and NMR spectroscopy for NABG detection and quantification.
Biological Properties of NABG
Several studies have shown that NABG can inhibit the growth of human breast cancer cells and the receptor binding of the Human Influenza Virus H1N1, making it a potential candidate for drug development. In addition, NABG has also been used successfully in the modification of different types of surfaces, thus increasing their antifungal and antibacterial properties. Animal studies using NABG for drug treatment showed reduced toxicity when compared to other chemotherapeutic drugs.
Toxicity and Safety in Scientific Experiments
According to published research, NABG has low toxicity, and it can be safely handled under standard laboratory conditions. However, as with any chemical compound, prolonged exposure to high concentrations of NABG can cause adverse health effects. Therefore, it should be handled with care and adhering to proper safety protocols in scientific experiments.
Applications in Scientific Experiments
NABG has found widespread use in several scientific research fields, including drug development, nanotechnology, materials science, and supramolecular chemistry. It can be used in the preparation of synthetic vaccines and the modification of biomolecules. Furthermore, it can be used in the development of nanocarriers for targeted drug delivery.
Current State of Research
NABG is a commercially available compound, and several research studies have focused on the synthesis, characterization, and applications of NABG in different scientific fields. More recently, studies have reported on the toxicity and biocompatibility of NABG, making it an exciting candidate for drug development applications.
Potential Implications in Various Fields of Research and Industry
NABG has the potential to revolutionize several research fields and industries by enabling the development of novel chemical compounds and surfaces with unique properties. It can be used to improve the solubility of drugs, making them more effective in combating diseases. NABG holds promise in the development of nanocarriers for targeted drug delivery and the modification of biomolecules.
Limitations and Future Directions
While research on the application of NABG in different scientific fields continues, certain limitations remain. These include its high production cost and limited availability in certain regions, as well as its high sensitivity to the environment (pH, temperature, and presence of metal ions). Currently, investigations on the biocompatibility and toxicity of NABG are ongoing, which should provide more insight into its potential applications in the healthcare and biomedical fields.
Future Directions for NABG Research include:
1. Developing improved and more efficient synthetic routes for NABG.
2. Studying the potential use of NABG in drug design and development.
3. Exploring the potential applications of NABG in nanotechnology.
4. Investigating the use of NABG in supramolecular chemistry.
5. Studying the biocompatibility and toxicity of NABG in animal models.
6. Developing new analytical techniques for NABG detection and quantification.
7. Exploring the potential use of NABG in tissue engineering and regenerative medicine.
8. Studying the effect of NABG in reducing the toxicity of chemotherapeutic drugs.
9. Investigating the use of NABG in the modification of biomolecules.
10. Studying NABG's potential applications in material science and engineering.
CAS Number | 80887-27-0 |
Product Name | 2-Acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranosyl Azide |
IUPAC Name | N-[(2R,4aR,6R,7R,8R,8aS)-6-azido-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide |
Molecular Formula | C22H24N4O5 |
Molecular Weight | 424.46 g/mol |
InChI | InChI=1S/C22H24N4O5/c1-14(27)24-18-20(28-12-15-8-4-2-5-9-15)19-17(30-21(18)25-26-23)13-29-22(31-19)16-10-6-3-7-11-16/h2-11,17-22H,12-13H2,1H3,(H,24,27)/t17-,18-,19-,20-,21-,22-/m1/s1 |
InChI Key | FVNJPKGJMMREOM-CGXUPHRESA-N |
SMILES | CC(=O)NC1C(C2C(COC(O2)C3=CC=CC=C3)OC1N=[N+]=[N-])OCC4=CC=CC=C4 |
Canonical SMILES | CC(=O)NC1C(C2C(COC(O2)C3=CC=CC=C3)OC1N=[N+]=[N-])OCC4=CC=CC=C4 |
Isomeric SMILES | CC(=O)N[C@@H]1[C@H]([C@H]2[C@@H](CO[C@H](O2)C3=CC=CC=C3)O[C@H]1N=[N+]=[N-])OCC4=CC=CC=C4 |
CAS No: 80887-27-0 MDL No: MFCD23104224 Chemical Formula: C22H24N4O5 Molecular Weight: 424.46 |
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