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10022-13-6 , Tetra-O-acetyl-2-deoxy-2-phthalimido-b-D-glucopyranoside, CAS:10022-13-6

10022-13-6 , Tetra-O-acetyl-2-deoxy-2-phthalimido-b-D-glucopyranoside,
C22H23NO11 / 477.42



The interaction of 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-b-D-glucopyranoside with DNA is selective for the hydroxyl group and for the stacking of its glycosidic bonds. The data obtained from the spectra show that this compound interacts with the sugar moiety of nucleosides to yield a product with a lower melting point. The binding constants are high and the yields are low.

1,3,4,6-Tetra-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranose is a common building block in carbohydrate chemistry that is widely utilized in scientific experiments. Its structure comprises a phthalimido group and a glucose residue that are linked with an acetyl function at position 4 and 6 of the saccharide ring. This paper aims to provide a comprehensive review of the physical and chemical properties, synthesis, 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, as well as future directions of 1,3,4,6-Tetra-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranose.

Definition and Background

1,3,4,6-Tetra-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranose, also called N-phthalyl-2-deoxy-2-acetamido-D-glucopyranosylamine, is a significant disaccharide derivative commonly used in chemical and biological research. This molecule is a key intermediate in the synthesis of oligosaccharides, glycopeptides, and glycolipids.

Synthesis and Characterization

1,3,4,6-Tetra-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranose can be synthesized using a few different methods, including the Mitsunobu reaction, a one-pot procedure using benzyl glycoside, as well as direct acylation of 2-deoxy-2-iodo-D-glucopyranosylamine with acetic anhydride. Characterization methods include NMR spectroscopy, mass spectrometry, IR spectroscopy, and X-ray crystallography.

Analytical Methods

Numerous analytical methods can be utilized to characterize 1,3,4,6-Tetra-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranose, including liquid chromatography-mass spectrometry (LC-MS), high-performance liquid chromatography (HPLC), nuclear magnetic resonance (NMR) spectroscopy, and infrared (IR) spectroscopy. Combining these techniques allows scientists to identify and quantify the exact structure of the molecule.

Biological Properties

Preliminary research indicates that 1,3,4,6-Tetra-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranose may have potential applications in the treatment of cancer, autoimmune diseases, and other inflammatory conditions. It has also been shown to enhance the immune response in vitro and in vivo. However, further studies are needed to determine its precise mechanism of action on biological systems.

Toxicity and Safety in Scientific Experiments

The toxicity of 1,3,4,6-Tetra-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranose is relatively low as it has been reported to have low adverse effects on the cells and animals in the laboratory. However, researchers should take precautions when handling this compound, including wearing appropriate personal protective equipment and following established safety protocols.

Applications in Scientific Experiments

1,3,4,6-Tetra-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranose is a versatile compound that has numerous applications in scientific experiments. It can be used in the synthesis of oligosaccharides, glycopeptides, and glycolipids. It also has potential applications in immunology, neurology, and cancer research.

Current State of Research

Currently, research on 1,3,4,6-Tetra-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranose is mostly focused on its role as a building block in the synthesis of complex glycoconjugates. However, there is also growing interest in its potential application in cancer treatment as well as autoimmune and inflammatory disease.

Potential Implications in Various Fields of Research and Industry

Given its unique properties, 1,3,4,6-Tetra-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranose has potential applications in various fields of research and industry. In the field of drug discovery, it may be used to develop new therapeutics for cancer and other diseases. It can also be used as a component in vaccines, and as a contrast agent in medical imaging.

Limitations and Future Directions

One disadvantage of 1,3,4,6-Tetra-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranose is its relatively high cost. Future research should focus on developing more efficient and cost-effective methods for synthesizing this molecule. New biological studies may focus on understanding the structural and biological properties of this compound and developing a broader understanding of applications in fields related to biotechnology and medicine.

Future Directions

There are several future directions of research for 1,3,4,6-Tetra-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranose:

1. Investigating its application in vaccine development and medical imaging.

2. Combining this molecule with cancer cell targeting agents to produce more effective cancer treatment.

3. Conducting research to determine if the molecule can optimize the immune response, thus finding potential application in immunotherapeutic regimes.

4. Developing more cost-effective and efficient methods of synthesizing this molecule.

5. Investigating the use of this molecule in the creation of innovative carbohydrate-based materials.

6. Exploring potential therapeutic applications in the field of neurology.

7. Investigating the molecule’s potential as a tool in the development of diagnostic assays for various diseases.

8. Exploring its potential as a delivery agent for therapeutics.

9. Conducting further research into its mechanism of action in biological systems.

10. Exploring its biocompatibility and safety which can be utilized further in biomedical engineering.

CAS Number10022-13-6
Product Name1,3,4,6-Tetra-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranose
IUPAC Name[(2R,3S,4R,5R,6S)-3,4,6-triacetyloxy-5-(1,3-dioxoisoindol-2-yl)oxan-2-yl]methyl acetate
Molecular FormulaC22H23NO11
Molecular Weight477.42 g/mol
Synonyms2-Deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-β-D-glucopyranose 1,3,4,6-Tetraacetate;
Canonical SMILESCC(=O)OCC1C(C(C(C(O1)OC(=O)C)N2C(=O)C3=CC=CC=C3C2=O)OC(=O)C)OC(=O)C
Isomeric SMILESCC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC(=O)C)N2C(=O)C3=CC=CC=C3C2=O)OC(=O)C)OC(=O)C
CAS No: 10022-13-6 Synonyms: 2-Deoxy-2-N-phthalimido-1,3,4,6-tetra-O-acetyl-b-D-glucopyranose MDL No: MFCD00080781 Chemical Formula: C22H23NO11 Molecular Weight: 477.42
References: 1. Am. Che. Soc. Sym. Ser., 1976, 39, p190


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