Synthesis method of astragaloside

A synthesis method and technology of astragaloside IV, applied in the fields of organic chemical methods, steroids, bulk chemical production, etc., can solve the problems of difficulty in synthesis of astragaloside IV, no successful reports, etc., and achieve the goal of promoting the research of active mechanism. Effect

Active Publication Date: 2017-06-13
JIANGXI NORMAL UNIVERSITY
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Problems solved by technology

[0008] This shows that astragaloside IV is difficult to synthesize

Method used

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  • Synthesis method of astragaloside
  • Synthesis method of astragaloside
  • Synthesis method of astragaloside

Examples

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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 synthesis method of astragaloside. The synthesis method of the astragaloside comprises the following steps of using protecting groups R1 for protecting 3-site hydroxy and 6-site hydroxy of cycloastragenol; after using protecting groups R2 for protecting 16- site hydroxy and 25- site hydroxy, removing the protecting groups R1 for the 3- site hydroxy and the 6- site hydroxy, and obtaining a compound 4; using a protecting group R3 for protecting 3- site hydroxy of the compound 4, and obtaining a compound 5; carrying out glycosylation on the compound 5, then removing the protecting group R3 for the 3- site hydroxy, continuously carrying out glycosylation, and obtaining a compound 8; removing all protecting groups to obtain the astragaloside. According to the synthesis method of the astragaloside provided by the invention, the astragaloside is high-efficiently and high-stereoselectively prepared, a gap in the prior art is filled, and the progresses of the activity mechanism research of astragalus membranaceus saponins and the medicinal development thereof are greatly improved.

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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IPC IPC(8): C07J53/00
CPCC07B2200/07C07J53/004Y02P20/55
Inventor 孙建松廖进喜刘婷
Owner JIANGXI NORMAL UNIVERSITY
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