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Benzo-dihydropyran glycoside derivatives

A technology of chroman and derivatives, which is applied in the field of chroman derivatives, and can solve the problems of vitamin E reduction, low activity, and loss of antioxidant activity

Inactive Publication Date: 2005-11-23
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, since the phenolic hydroxyl group on the chroman ring of the parent vitamin E is very important for antioxidant activity, destroying the phenolic hydroxyl group will greatly reduce or lose the antioxidant activity of vitamin E
The structure reported in the above literature is due to the destruction of the hydroxyl group on the chroman ring, which leads to the low activity of these structures.
In addition, the direct glycosylation of vitamin E will cause vitamin E to be easily oxidized, and a series of oxidation by-products with the following structure will be generated, resulting in a decrease in yield

Method used

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  • Benzo-dihydropyran glycoside derivatives

Examples

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Embodiment 1

[0069] Synthesis of Compound 1 and Compound 3:

[0070] (1) Synthesis of 1,4-p-methoxy-2,3-dimethylbenzene:

[0071] 2,3-Dimethylhydroquinone (1.38g, 0.01mol) was dissolved in 8mL dimethylsulfoxide (DMSO), and methyl iodide (3.2mL, 7.3g, 0.05mol) and KOH (4g, 0.07mol) solid, reacted at room temperature for 5 hours, and thin-plate chromatography (TLC) showed that the reaction had ended. Add 20 mL of water and stir for 5 minutes, then add CH 2 Cl 2 Extracted several times, combined the dichloromethane extracts, successively washed with saturated Na 2 S 2 o 3 Wash with saturated solution and saturated brine, and dry over anhydrous magnesium sulfate. Filtration, the organic phase was evaporated under reduced pressure to remove the solvent, the concentrate was separated through a short column, and the 2 Cl 2 A mixed solvent (volume ratio of 2:1) was eluted, and the eluent was evaporated under reduced pressure to remove the solvent to obtain white crystal 1,4-p-methoxy-2,3-d...

Embodiment 2

[0128] Synthesis of Compound 2 and Compound 4:

[0129] (1) Synthesis of 1,4-p-methoxy-2,6-dimethylbenzene:

[0130] Sodium nitrite (34g, 0.50mol) was dissolved in 100mL of water under an ice bath, and 200g of crushed ice was dropped into it, and 100mL of sodium metabisulfate (Na 2 S 2 o 5 ) in aqueous solution (35%, w / v), and then add 20 mL of glacial acetic acid. After 3 minutes, 25 mL of concentrated ammonia (spgr0.8) was added. After reacting for 30 minutes, slowly add 400 mL of an aqueous solution of potassium permanganate (12.6 g, 0.079 mol) dropwise, continue stirring for 1 hour and filter, and pour the obtained purple filtrate into 800 mL of a saturated KCl solution under stirring. After stirring for 1 hour, filter to obtain Fermi's salt (Fremy's salt). The freshly prepared Fermi salt was dissolved in water at 0°C, and 400 mL of a methanol solution of 2,6-dimethylphenol (4.5 g, 0.037 mol) was slowly added dropwise with stirring. After reacting at room temperature...

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Abstract

The invention relates to a benzo-dihydropyran glycoside derivatives whose structure is illustrated by formula (I) disclosed in the specification, the derivative is prepared through using corresponding hydroquinone or hydroxybenzene as starting raw material, then carrying out methylation, 1,2,3,4,substitution of phenyl ring by 6-penta-O-acetyl-beta-D-glucopyranose, benzene quinonization, hydrogen quinonization, cyclisation and alcoholysis. In formula (I), R1, R3 are selected from H, CH3 and one of (II), R2 is C1-C16 alkyl, R4 is H or CH3, wherein at least one of R1 and R3 is (III) but R1 and R3 cannot be (IV) at the same time.

Description

technical field [0001] The invention relates to a chroman dihydrocarbopyranoside derivative. Background technique [0002] Tocopherol compounds (vitamin E) are an important class of chroman derivatives. As the most outstanding antioxidant and free radical scavenger in organisms, vitamin E has been widely used in medicine, food, Feed, cosmetics and materials and other related industries. [0003] However, due to the poor water solubility of vitamin E or its analogues, its application is limited. Therefore, the introduction of hydrophilic groups on vitamin E to improve its water solubility, so as to obtain hydrophilic, lipophilic and amphipathic vitamin E, will greatly promote its wider application. Literature Carbohydrate Research, 23, 299, 1997, and 72, 325, 2000 reported that glucose or its oligosaccharides and vitamin E were used to directly synthesize vitamin E glucosyloxyglycoside under the catalysis of Lewis acid respectively, and its structure is as follows: [0004...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/04
Inventor 陈国荣何立让・皮埃尔・普拉利
Owner EAST CHINA UNIV OF SCI & TECH
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