Method for synthesizing iso-astragaloside IV

A technology for astragaloside IV and a synthesis method, which is applied in the production of steroids, bulk chemicals, organic chemistry, etc., can solve the problems of difficulty in synthesizing isostragaloside IV, no success, etc., and achieves research on the active mechanism and its medicine. Development process, high stereoselectivity effect

Active Publication Date: 2017-07-14
JIANGXI NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Method for synthesizing iso-astragaloside IV
  • Method for synthesizing iso-astragaloside IV
  • Method for synthesizing iso-astragaloside IV

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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 iso-astragaloside IV. The method comprises protecting the 3th site hydroxyl group of cycloastragenol by a protecting group R1, protecting the 6th site and 16th site hydroxyl groups through a protecting group R2 to obtain a compound 3, carrying out glycosylation on the compound 3, removing the protecting group R1 at the 3th site, carrying out glycosylation to obtain a compound 8, and removing all the protecting groups to obtain iso-astragaloside IV 1. The method is an efficient and highly stereoselective iso-astragaloside IV synthesis method, provides enough raw materials for iso-astragaloside IV research and application, provides reference for synthesis of iso-astragaloside compounds, fills the gap in the prior art and greatly promotes activity mechanism study of the astragaloside compounds and 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 Applications(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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