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132748-02-8 , Tetra-O-benzyl-D-galactopyranosyl trichloroacetimidate , CAS: 132748-02-8

132748-02-8 ,Tetra-O-benzyl-D-galactopyranosyl trichloroacetimidate ,
CAS:132748-02-8
C36H36Cl3NO6 / 685.03
MFCD07369660

2,3,4,6-Tetra-O-benzyl-D-galactopyranosyl trichloroacetimidate

四苄基-D-半乳糖三氯乙酰亚胺酯,

2,3,4,6-Tetra-O-benzyl-D-galactopyranosyl trichloroacetimidate is a glycosyl donor molecule that is used in glycosylation reactions. It belongs to the class of imidates, which are glycosyl donors commonly used in organic synthesis. The molecule has four benzyl groups and one trichloroacetamide attached to the galactopyranose ring. This compound has been shown to be a useful building block for the synthesis of oligosaccharides and glycoconjugates.

Synthesis and Characterization:

The synthesis of 2,3,4,6-Tetra-O-benzyl-D-galactopyranosyl trichloroacetimidate can be achieved by various methods such as benzylations, imidation, acylations, and deprotection reactions. The most widely used method is the benzyl imidate method, which involves the reaction of benzyl alcohol with trichloroacetonitrile, followed by the addition of galactopyranosyl acetate and triethylamine. Characterization of 2,3,4,6-Tetra-O-benzyl-D-galactopyranosyl trichloroacetimidate can be done using various analytical techniques such as infrared spectroscopy, nuclear magnetic resonance spectroscopy, mass spectrometry, and high-performance liquid chromatography.

Analytical Methods:

Various analytical methods can be used to analyze 2,3,4,6-Tetra-O-benzyl-D-galactopyranosyl trichloroacetimidate and its derivatives. The most commonly used methods are high-performance liquid chromatography (HPLC), gas chromatography-mass spectrometry (GC-MS), and infrared (IR) spectroscopy. These techniques allow accurate identification, quantification, and purity analysis of the compound.

Biological Properties:

2,3,4,6-Tetra-O-benzyl-D-galactopyranosyl trichloroacetimidate has been shown to possess various biological properties. Studies have shown that this compound can act as an antiproliferative agent against certain types of cancer cells. It has also been reported to exhibit antibacterial and antifungal activity. In addition, this compound has been shown to have promising antiviral activity against human cytomegalovirus.

Toxicity and Safety in Scientific Experiments:

Studies have shown that 2,3,4,6-Tetra-O-benzyl-D-galactopyranosyl trichloroacetimidate is relatively safe for use in scientific experiments. However, like any chemical compound, it can pose certain risks if not handled properly. It is important to use this compound in a well-ventilated area and avoid contact with skin, eyes, and clothing.

Applications in Scientific Experiments:

The unique properties of 2,3,4,6-Tetra-O-benzyl-D-galactopyranosyl trichloroacetimidate make it a valuable tool for the synthesis of oligosaccharides and glycoconjugates. It has been used in the synthesis of various biologically active molecules such as antitumor agents, antibiotics, and antiviral agents. In addition, it has also been used as a glycosylation reagent in the preparation of functionalized molecules for use in various applications, such as drug delivery and diagnostics.

Current State of Research:

Research on 2,3,4,6-Tetra-O-benzyl-D-galactopyranosyl trichloroacetimidate is ongoing, and new applications and synthesis methods are being developed. Recent studies have focused on the synthesis of glycoconjugates and oligosaccharides with potential therapeutic applications.

Potential Implications in Various Fields of Research and Industry:

The unique properties of 2,3,4,6-Tetra-O-benzyl-D-galactopyranosyl trichloroacetimidate make it a valuable tool in various fields of research and industry. It has potential applications in the synthesis of new drugs, diagnostics, and biomaterials. Furthermore, it has wide-ranging potential uses in the food and cosmetic industries.

Limitations and Future Directions:

Despite its potential, there are some limitations to the use of 2,3,4,6-Tetra-O-benzyl-D-galactopyranosyl trichloroacetimidate. For example, its high cost and low availability make it difficult to use in large-scale industrial applications. However, ongoing research is focusing on developing new synthesis methods and improving the compound's stability and storage properties. Additionally, there is a need for further research to elucidate the full range of biological activities of 2,3,4,6-Tetra-O-benzyl-D-galactopyranosyl trichloroacetimidate and its potential uses in various fields.

Future Directions:

1. Development of new synthesis methods to improve efficiency and reduce costs.

2. Investigation of the full range of biological activities of 2,3,4,6-Tetra-O-benzyl-D-galactopyranosyl trichloroacetimidate.

3. Improvement of stability and storage properties to increase shelf life.

4. Application to the synthesis of new drugs and biomaterials with potential therapeutic applications.

5. Investigation of its potential use in the food and cosmetic industries.

6. Exploration of its potential use as an antibacterial, antifungal, and antiviral agent.

7. Development of new analytical methods for accurate quantification and purity analysis.

8. Investigation of the mechanism of action of 2,3,4,6-Tetra-O-benzyl-D-galactopyranosyl trichloroacetimidate in biological systems.

9. Investigation of its potential use in the synthesis of glycoconjugates and oligosaccharides with therapeutic applications.

10. Improvement of glycosylation reactions using 2,3,4,6-Tetra-O-benzyl-D-galactopyranosyl trichloroacetimidate to increase yields and reduce side reactions.

CAS Number

132748-02-8

Product Name

2,3,4,6-Tetra-O-benzyl-D-galactopyranosyl trichloroacetimidate

IUPAC Name

2,2,2-trichloro-N-[(3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]acetamide

Molecular Formula

C₃₆H₃₆Cl₃NO₆

Molecular Weight

685.03

InChI

InChI=1S/C36H36Cl3NO6/c37-36(38,39)35(41)40-34-33(45-24-29-19-11-4-12-20-29)32(44-23-28-17-9-3-10-18-28)31(43-22-27-15-7-2-8-16-27)30(46-34)25-42-21-26-13-5-1-6-14-26/h1-20,30-34H,21-25H2,(H,40,41)/t30-,31+,32+,33-,34?/m1/s1

SMILES

C1=CC=C(C=C1)COCC2C(C(C(C(O2)NC(=O)C(Cl)(Cl)Cl)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5

Synonyms

2,3,4,6-Tetrakis-O-(phenylmethyl)-D-galactopyranose 2,2,2-Trichloroethanimidate;


CAS No: 132748-02-8 MDL No: MFCD07369660 Chemical Formula: C36H36Cl3NO6 Molecular Weight: 685.03


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