Method for synthesizing icariin by glucosidation of dehydrated epimedium herb

A technology of icariin and chemical synthesis, which is applied in the direction of chemical instruments and methods, sugar derivatives, sugar derivatives, etc., can solve the problems of long reaction process, low yield, low sugar yield, etc., and achieve selective The effect of improving performance, enhancing selectivity and reducing cost

Active Publication Date: 2011-06-15
内蒙古源宏精细化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] In the method (1), the reaction process is long and the yield is low, especially when the glycosylation reaction uses silver nitrate as a reagent, and the overall sugar yield is low
[0014] Natural plant extraction is difficult to obtain the product of high content in method (2)
[0015] In method (3), a single glycosylation reaction is reported. The other hydroxyl groups of flavonoids are protected first, followed by glycosylation. There is no report on the glycosylation of two hydroxyl groups when the hydroxyl group is unprotected.

Method used

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  • Method for synthesizing icariin by glucosidation of dehydrated epimedium herb
  • Method for synthesizing icariin by glucosidation of dehydrated epimedium herb
  • Method for synthesizing icariin by glucosidation of dehydrated epimedium herb

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] (a) Put 200g of dry DMF into a 300ml reaction bottle, then add 20g (54.29mmol) of dehydrated icariin, stir and dissolve, add 18.4g (124.64mmol) of strontium carbonate, stir at room temperature for one hour, add α -Bromotetraacetyl-D-glucopyranose 24.6g (59.83mmol), continue to stir at room temperature for 48h, remove strontium bromide by filtration, concentrate the filtrate to dryness under reduced pressure, add 1000g of ethyl acetate, and then use 1% 500 g of hydrobromic acid aqueous solution was washed, washed with water, dehydrated with sodium sulfate and then concentrated to dryness. Column chromatography obtained 29.7 g of 7-O-β-tetraacetyl-D-glucopyranosyl anhydro-icarioside.

[0035] (b) Put 200g of dry dichloromethane into a 300ml reaction bottle, then add 29.7g of 7-O-β-tetraacetyl-D-glucopyranosyl dehydroicariside, stir to dissolve, then add Silver trifluoromethanesulfonate 10.8g and triethylamine 10ml (71.89mmol), after stirring at room temperature for one ho...

Embodiment 2

[0038] (a) Put 200g of dry acetonitrile into a 300ml reaction flask, then add 20g (54.29mmol) of dehydrated icariin, stir and dissolve, add 18.4g (124.64mmol) of strontium carbonate, and add α-bromotetraacetyl Base-D-glucopyranose 24.6g (59.83mmol), continued to stir at room temperature for 48h, filtered, the filtrate was concentrated to dryness under reduced pressure, added 1000g of ethyl acetate, then washed with 500g of 1% hydrobromic acid aqueous solution, washed with water, It was dehydrated with sodium sulfate and then concentrated to dryness. Column chromatography gave 20.9 g of 7-O-β-tetraacetyl-D-glucopyranosyl anhydro-icarioside.

[0039] (b) Put 200g of dry chloroform into a 300ml reaction bottle, then add 20.9g of 7-O-β-tetraacetyl-D-glucopyranosyl dehydroicariside, stir and dissolve, then add trifluoro Silver methanesulfonate 7.7g, stirred at room temperature for one hour, added 17.6g of α-bromotriacetyl-L-rhamnopyranose, continued to stir at room temperature for ...

Embodiment 3

[0042] (a) Put 200g of dry acetone into a 300ml reaction flask, then add 20g (54.29mmol) of dehydrated icariin, stir and dissolve, add 22.6g of strontium carbonate, add α-bromotetraacetyl-D- Glucopyranose 24.6g, stirred at 50°C for 48h, filtered, the filtrate was concentrated to dryness under reduced pressure, added 1000g of ethyl acetate, washed with water, dehydrated with sodium sulfate and concentrated to dryness, and obtained 7-O-β-tetraacetyl Base-D-glucopyranosyl dehydroicariside 27.9g.

[0043] (b) 200g of dry methylene chloride is dropped into a 300ml reaction flask, then 27.9g of 7-O-β-tetraacetyl-D-glucopyranosyl dehydroicariside is added, and after stirring and dissolving, three Silver fluoromethanesulfonate 12.8g and pyridine 8g, after stirring at room temperature for one hour, add α-bromotriacetyl-L-rhamnopyranose 18.2g, cool down to 0°C and stir for 24h, then remove silver bromide by filtration and pyridinium trifluoromethanesulfonate, the filtrate was concentra...

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Abstract

The invention relates to a method for synthesizing icariin by glucosidation of dehydrated epimedium herb. The conventional method for synthesizing icariin by glucosidation of dehydrated epimedium herb is low in selectivity. For solving the problem, the method uses strontium carbonate as a catalyst and comprises the following steps: dissolving dehydrated icaritin in an organic solvent; reacting the icaritin with alpha-bromotetraacetyl-D-glucopyranose in the presence of strontium carbonate to perform glucosidation at position-3; reacting the product of the glucosidation with alpha-bromotriacetyl-L-rhamnopyranoside in the presence of a silver trifluoromethanesulfonate catalyst to perform glucosidation at position-7; and performing deacetylation reaction to obtain icariin. The method is suitable to synthesize icariin.

Description

technical field [0001] The invention relates to a method for synthesizing epimedium monoside by dehydrating epimedium glucoside. Background technique [0002] Epimedium monoside is a plant that comes from the dry stems and leaves of the Berberidaceae Berberidaceae perennial herb Epimedium Brericrnuml that is wild in the wild bamboo forests of Hubei, Sichuan, Zhejiang and other provinces or in the crevices of mountain roads Extract. Epimedium is a traditional Chinese medicine tonic. It has the functions of nourishing yang and kidney, strengthening the disc bone, and dispelling rheumatism. Can effectively inhibit Staphylococcus, anti-aging. Icariin is one of its active ingredients, which can effectively improve the cardiovascular system, regulate endocrine, and improve endocrine. In addition, what deserves special attention is that Epimedium also has anti-cancer effects, and has been hailed as the most potential anti-cancer drug. Its structural formula (I) is as follows: ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/07C07H1/00
Inventor 王兵波张森
Owner 内蒙古源宏精细化工有限公司
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