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A kind of synthetic method of astragaloside IV

A synthetic method, the technology of astragaloside IV, applied in the direction of organic chemical methods, steroids, bulk chemical production, etc., can solve the problems of difficult synthesis of astragaloside IV, no successful reports, etc., and achieve the goal of advancing the research on the mechanism of activity Effect

Active Publication Date: 2018-02-09
JIANGXI NORMAL UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0008] This shows that astragaloside IV is difficult to synthesize, 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 astragaloside IV
  • A kind of synthetic method of astragaloside IV
  • A kind of synthetic method of astragaloside IV

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example 1

[0044] Example 1, the synthesis of astragaloside IV

[0045]

[0046] (1) Synthesis of cycloastragenol derivative 2 protected by 3 and 6 hydroxyl groups

[0047]

[0048] Under nitrogen protection, under the condition of 0 degrees Celsius, cycloastragenol (300mg, 0.61mmol), DMAP (160mg, 1.22mmol) and levulinic acid (350mg, 3.06mmol) were dissolved in dry dichloromethane (9mL), and then DCC (630mg, 3.06mmol) was added to the system, the system was slowly raised to room temperature, and stirred until TLC tracking showed that the reaction of the raw materials was complete, the reaction system was extracted with ethyl acetate, and sequentially washed with 1mol / l HCl, saturated sodium bicarbonate, saturated Washed with NaCl, dried over anhydrous sodium sulfate, filtered with suction, concentrated the crude product under reduced pressure, and then obtained white solid compound 2 (413 mg, 98.3%) by column chromatography: [α] D 25 =39.6 (c=1, CHCl 3 ); 1 H NMR (400MHz, CDCl ...

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Abstract

The invention discloses a method for synthesizing astragaloside IV, which comprises the following steps: protecting the 3-position and 6-position hydroxyl of cycloastragenol with a protecting group R1; protecting the 16-position and 25-position hydroxyl with a protecting group R2 and removing the 3-position and the 6-position protecting group R1 to obtain compound 4; protect the 3-position hydroxyl of compound 4 with protecting group R3 to obtain compound 5; carry out glycosylation reaction of compound 5, and then remove the 3-position protecting group R3 to continue glycosylation reaction to obtain compound 8; all protecting groups are removed to obtain astragaloside IV; the present invention has prepared astragaloside IV with high efficiency and high stereoselectivity, which fills the gap in the prior art, and will greatly promote the research on the activity mechanism of astragaloside compounds and its drug development process.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and more specifically relates to a preparation method of astragaloside 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 the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J53/00
CPCC07B2200/07C07J53/004Y02P20/55
Inventor 孙建松廖进喜刘婷
Owner JIANGXI NORMAL UNIV
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