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92420-89-8, Tri-O-acetyl-a-D-glucuronide methyl ester trichloroacetimidate, CAS:92420-89-8

92420-89-8, Tri-O-acetyl-a-D-glucuronide methyl ester trichloroacetimidate,
CAS:92420-89-8
C15H18Cl3NO10 / 478.66
MFCD02094293

2,3,4-Tri-O-acetyl-a-D-glucuronide methyl ester trichloroacetimidate

三乙酰基-a-D-葡萄糖醛酸甲酯三氯乙酰亚胺酯, 

2,3,4-Tri-O-acetyl-alpha-D-glucuronic Acid Methyl Ester, Trichloroacetimidate (TME) is a derivative of D-glucuronic acid, which is an important component of the extracellular matrix and plays a crucial role in biological processes such as cell adhesion, migration, and signaling. TME is synthesized by the reaction of D-glucuronic acid with trichloroacetonitrile in the presence of acetyl chloride and pyridine, followed by methanolysis.

Synthesis and Characterization

TME can be synthesized by a series of chemical reactions involving D-glucuronic acid, trichloroacetonitrile, acetyl chloride, and pyridine. The reaction products are purified by column chromatography and characterized by spectroscopic methods such as NMR and IR.

Analytical Methods

Analytical methods such as HPLC and GC-MS are commonly used for the quantification and identification of TME in biological and chemical samples. NMR and IR spectroscopy are used to confirm the identity and purity of the synthesized TME.

Biological Properties

TME has been shown to exhibit antitumor activity in vitro and in vivo. It inhibits the growth and proliferation of cancer cells by inducing cell cycle arrest and apoptosis. TME has also been reported to inhibit the migration and invasion of cancer cells by affecting the extracellular matrix.

Toxicity and Safety in Scientific Experiments

TME has shown low toxicity in animal studies. However, further studies are required to establish its long-term safety and toxicity profile.

Applications in Scientific Experiments

TME is a useful reagent in the synthesis of oligosaccharides and glycoconjugates. It can be used in the preparation of glycosyl donors and acceptors for glycosylation reactions. TME derivatives can also be used as substrates for glycosidases.

Current State of Research

Research on TME has focused on its synthesis and characterization, its biological properties as an antitumor agent, and its applications in organic synthesis.

Potential Implications in Various Fields of Research and Industry

TME has potential implications in the fields of organic synthesis, glycobiology, and cancer therapy. Its use as a glycosylation reagent and its antitumor activity make it a promising molecule for drug development.

Limitations and Future Directions

The limitations of TME include its low solubility in water, which limits its use in biological applications. Further research is needed to improve its solubility and to establish its long-term safety and toxicity profile. Future directions include the synthesis of new TME derivatives with improved properties and the development of TME-based drugs for cancer therapy.

List of Future Directions:

- Synthesis of TME derivatives with improved solubility and biological activity

- Development of TME-based drugs for cancer therapy

- Identification of the molecular targets of TME in cancer cells

- Study of the mode of action of TME in inhibiting cancer cell proliferation and migration

- Investigation of the potential of TME as a diagnostic tool for cancer

- Evaluation of the safety and efficacy of TME in clinical trials

- Study of the role of TME and its derivatives in glycobiology and carbohydrate chemistry

- Use of TME as a tool for the synthesis of complex oligosaccharides

- Study of the interactions of TME with biological molecules such as proteins and carbohydrates

- Development of new analytical methods for the quantification and identification of TME in biological samples.

CAS Number92420-89-8
Product Name2,3,4-Tri-O-acetyl-alpha-D-glucuronic Acid Methyl Ester, Trichloroacetimidate
IUPAC Namemethyl (2S,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxane-2-carboxylate
Molecular FormulaC₁₅H₁₈Cl₃NO₁₀
Molecular Weight478.66
InChIInChI=1S/C15H18Cl3NO10/c1-5(20)25-8-9(26-6(2)21)11(27-7(3)22)13(28-10(8)12(23)24-4)29-14(19)15(16,17)18/h8-11,13,19H,1-4H3/t8-,9-,10-,11+,13+/m0/s1
SMILESCC(=O)OC1C(C(OC(C1OC(=O)C)OC(=N)C(Cl)(Cl)Cl)C(=O)OC)OC(=O)C
SynonymsMethyl-(2,3,4-tri-O-acetyl-α-D-glucopyranosyl Trichloroacetimidate)uronate;


CAS No: 92420-89-8 Synonyms: Methyl-(2,3,4-tri-O-acetyl-a-D-glucopyranosyl trichloroacetimidate)uronateMethyl-2,3,4-tri-O-acetyl-1-O-trichloroacetimidoyl-a-D-glucopyranosyluronate 

 MDL No: MFCD02094293 Chemical Formula: C15H18Cl3NO10 Molecular Weight: 478.66


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