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A kind of synthetic method of isoastragaloside IV

A technique for the synthesis of astragaloside IV, which is applied in the production of steroids, organic chemistry, bulk chemicals, etc., can solve problems such as failure to find success and difficulty in synthesizing isoastragloside IV, and promote the research on the mechanism of activity and its medicine Progress of development, effect of high stereoselectivity

Active Publication Date: 2020-01-03
JIANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It can be seen that the synthesis of isoastragloside IV is difficult, and there has been no successful report at home and abroad so far

Method used

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  • A kind of synthetic method of isoastragaloside IV
  • A kind of synthetic method of isoastragaloside IV
  • A kind of synthetic method of isoastragaloside IV

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Experimental program
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Embodiment 1

[0039] Synthesis of isoastragaloside IV,

[0040]

[0041] (1) Synthesis of cycloastragenol derivative 2 protected by the 3-hydroxyl group,

[0042]

[0043] Under nitrogen protection, cycloastragenol (400mg, 0.82mmol) was dissolved in dry DMF, and TBSCl (489mg, 3.3mmol) and imidazole (333mg, 4.9mmol) were added to the system, and stirred at room temperature until TLC tracking showed that the reaction of the raw materials was complete , the reaction system was extracted with ethyl acetate, washed successively with 1mol / l HCl, saturated sodium bicarbonate, and saturated NaCl, dried over anhydrous sodium sulfate, filtered with suction, concentrated the crude product under reduced pressure, and then obtained a white solid compound by column chromatography 2 (76.8%): [α] D 25 =30.5 (c=1, CHCl 3 ); 1 H NMR (400MHz, CDCl 3 )δ4.67(dd, J=7.6,14.4Hz,1H),3.72(dd,J=6.0,8.0Hz,1H),3.51(td,J=3.6,9.6Hz,1H),3.25(dd,J =4.8,10.0Hz,1H),2.59(dd,J=10.4,21.6Hz,1H),2.31(d,J=8.0Hz,1H),2.0...

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Abstract

The invention discloses a method for synthesizing isoastragaloside IV, which comprises the following steps: converting the 3-position hydroxyl group of cycloastragenol into a protecting group R 1 Protection, the 6- and 16-position hydroxyl groups are protected by R 2 After protection, compound 3 is obtained, and compound 3 is subjected to glycosylation reaction, and then the 3-position protecting group R is removed 1 , continue the glycosidation reaction to obtain compound 8, and remove all protecting groups to obtain isoastragaloside IV. The application provides sufficient raw materials, provides reference for the synthesis of isoastragloside compounds, fills in the gaps in the prior art, and will greatly promote the research on the activity mechanism of astragaloside compounds and the process of drug development.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and more specifically relates to a preparation method of isoastragloside IV. Background technique [0002] Astragalus is the first tonic and belongs to the genus Astragalus in the leguminous family. In recent years, with the development of modern separation and identification technology, a large number of triterpenoid saponins, flavonoids and polysaccharides have been isolated from Astragalus membranaceus. Later biochemical experiments showed that the medicinal effects of Astragalus membranaceus are mainly manifested through Astragalus saponins. Recent studies have shown that astragalus saponins have shown very promising medicinal prospects in terms of immune regulation, hypoglycemia, improvement of insulin resistance, anti-tumor, regulation of the cardiovascular system, anti-virus, and antioxidant activities. Among the saponins, the activities of astragaloside IV and isoastragaloside IV are t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J53/00
CPCC07J53/004Y02P20/55
Inventor 廖进喜孙建松刘婷
Owner JIANGXI NORMAL UNIV
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