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Synthetic method of Lewis-X

A synthesis method and compound technology, applied in the synthesis field of Lewis oligosaccharide-X, can solve the problems of time-consuming, labor-consuming, cost, etc.

Active Publication Date: 2018-07-20
FOSHAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In order to find more active compounds, there are many reports on the research on the synthesis of Lewis-X related oligosaccharides and mimics, however, all the reported methods are time-consuming, labor-intensive and costly

Method used

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  • Synthetic method of Lewis-X
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Embodiment Construction

[0025] The present invention will be further described below in combination with specific embodiments.

[0026] Synthesis of compound 2 from compound 1

[0027] Compound 1 (2.9g, 2mmol) was dissolved in anhydrous tetrahydrofuran (50mL), then TBAF (780mg, 3mmol) was added, and under nitrogen protection, the reaction was stirred at room temperature for 4 hours; after removing the solvent, the residue was subjected to a silica gel column Chromatography was purified, and the eluent was a mixture of n-hexane / ethyl acetate volume ratio 1:1; the purified product was dissolved in dichloromethane (30ml), and anhydrous potassium carbonate (100mg) and trichloroacetonitrile ( 1eq), under nitrogen protection, stirred at room temperature for 2 hours; filtered to remove the solid, the filtrate was distilled under reduced pressure; in the presence of boron trifluoride ether (30mg), the residue was mixed with HO(CH 2 ) 8 PC 6 h 4 OMe (1eq) was subjected to a coupling reaction in anhydrous ...

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Abstract

The invention relates to a synthetic method of Lewis-X. Lewis-X is synthesized from a compound 1 as a starting material. Through the adoption of the synthetic method, the defects that time and labor are consumed and synthetic cost is high in the prior art are overcome, and a new synthesis idea is provided for synthesis of Lewis-X and Lewis-X derivatives.

Description

technical field [0001] The present invention relates to a synthetic method of Lewis oligosaccharide-X. Background technique [0002] Carbohydrate recognition has been shown to be involved in many biological processes. E-selectin is expressed in cytokine-stimulated endothelial cells and plays an important role in the trafficking of neutrophils to sites of inflammation. The tetrasaccharide sialylated Lewis oligosaccharide-X is distributed on the surface of neutrophils and has been confirmed to be a ligand recognized by E-selectin. Since the interaction between sialylated Lewis-X and E-selectin is critical for the initial phase of neutrophil infiltration at inflammatory sites, Lewis-X and its derivatives can block this This interaction can serve as a new anti-inflammatory and anti-tumor agent. [0003] In order to find more active compounds, there are many reports on the research on the synthesis of Lewis-X related oligosaccharides and mimics, however, all the reported metho...

Claims

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Application Information

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IPC IPC(8): C07H15/18C07H1/00
CPCC07H1/00C07H15/18
Inventor 丁毅力李紫元王丙云
Owner FOSHAN UNIVERSITY