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Method for preparing activity constituent rosavin derivates in rhodiola rosea and application

A synthesis method and reaction technology, applied in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., can solve the problems of high cost, unsuitable for mass production, etc.

Inactive Publication Date: 2009-06-17
上海药谷药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It has been reported in the literature that rosavins are obtained from plant cell culture, but the cost is high and it is not suitable for mass production

Method used

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  • Method for preparing activity constituent rosavin derivates in rhodiola rosea and application
  • Method for preparing activity constituent rosavin derivates in rhodiola rosea and application
  • Method for preparing activity constituent rosavin derivates in rhodiola rosea and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Example 1 Glycosyl Donor Synthesis

[0019] 1) 2,3,4,5-Tetra-O-benzoylglucopyranoside Synthesis

[0020] At room temperature, add 170ml of dichloromethane into a 500ml three-neck round bottom flask with mechanical stirring, and start stirring. Glucose tetrabenzoate (34 g, 0.057 mol) was added and stirred until the solids were completely dissolved. Trichloroacetonitrile (10ml, 0.09mol) was added, and then DBU (1,8-diazabicyclo[5.5.4]-7-undecene), (0.68ml, 0.0046mol) was added by syringe. The reaction progress was monitored by TLC, and after the reaction was completed, the column was quickly purified.

[0021] 2) 2,3,4-tri-O-benzoyl-[6-O-(2',3',4'-tri-O-acetyl)-L-arabinofuranosyl]-D-pyridine glucopyranose trichloroacetimidate

[0022] (1) Synthesis of 6'-O-Tr-2', 3', 4'-tri-benzoyl-glucopyranosyl imidate

[0023] a) Synthesis of 6-O-triphenylmethyl-glucose

[0024] Dissolve D-glucose (180.16g, 1.0mol) in pyridine (1800ml), add TrCl (362g, 1.3mol) and DMAP (1.833...

example 2

[0060] Synthesis of Example 2 Fully Protected Rosavins

[0061] 1) Fully protected Rosin Synthesis

[0062] Add cinnamyl alcohol, perbenzoylated glucosiminate, and 4A molecular sieves into an eggplant-shaped bottle, vacuumize, and fill with argon; the above operation is repeated once. Add anhydrous dichloromethane, stir at room temperature for 30 minutes, then cool in an ice-salt bath, add TMSOTf / dichloromethane solution dropwise in batches, react at low temperature for 20 minutes, rise to room temperature and quench with triethylamine. The reaction process was monitored by TLC, the reaction solution was filtered, the filter residue was washed with dichloromethane, the filtrate was concentrated to dryness under reduced pressure, separated by silica gel column chromatography, the eluent containing the product was concentrated to dryness under reduced pressure, and dried by a vacuum pump to obtain a light yellow foam solid product. The yield is 50-80%

[0063] (2) Fully p...

example 3

[0082] Example 3 Synthesis of Rosavins

[0083] 1) Rosin Synthesis

[0084] Add the full-protection product, dichloromethane, and stir to dissolve in an eggplant-shaped bottle, then add methanol, and then add a catalytic amount of sodium methoxide, and stir overnight at room temperature. TLC monitors the reaction process, and the reaction solution is concentrated to dryness under reduced pressure, separated by silica gel column chromatography, and purified by column chromatography (CHCl 3 / MeOH) to obtain highly pure white solid rosin.

[0085] (2) Rosarin Synthesis

[0086] Add the full-protection product, dichloromethane, and stir to dissolve in an eggplant-shaped bottle, then add methanol, and then add a catalytic amount of sodium methoxide, and stir overnight at room temperature. TLC monitors the reaction process, and the reaction solution is concentrated to dryness under reduced pressure, separated by silica gel column chromatography, and purified by column chromat...

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Abstract

The invention relates to a synthesis method for Beta-(E)-cinnamic alcohol glycosides (Rosavin derivatives). The method comprises: carrying out the glycoside reaction on Cinnamic alcohol and different varieties of glycosyl trichloroacetimidate, and then removing a protective group, so as obtain Beta-(E)-cinnamic alcohol glycosides. The method has easily obtained raw materials, moderate reaction conditions and high product purity. The method is not reported in a document. Therefore, the synthesis method is a novel method for artificially synthesizing cinnamic alcohol glycoside.

Description

technical field [0001] The present invention relates to a series of synthetic methods of cinnamyl alcohol glycosides (Rosavin derivatives) Background technique [0002] Rhodiola rosea (Rhodiola rosea L.), also known as "Rhodiola rosea", belongs to the genus Rhodiola (Crassulaceae) of Crassulaceae, a perennial herb or subshrub. About 70cm high, the flowers are yellow in color, and its roots and rhizomes are used medicinally. It mainly grows in arid sandy land and high-altitude mountains at an altitude of about 1000-5000 meters in Europe and Asia. It is named after its newly cut rhizomes that emit a rose-like aroma. Rhodiola rosea is famous for its effects of eliminating fatigue, anti-hypoxia, anti-depression, anti-microwave radiation and delaying aging. It is a traditional herbal medicine known as "Plateau Ginseng". Pharmacological experimental studies have confirmed that the main active ingredients of Rhodiola rosea are salidroside (salidroside) and three of its unique cin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/18C07H1/00
CPCY02P20/55
Inventor 惠永正杨志奇王爱玲
Owner 上海药谷药业有限公司
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