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Astramembrannin II synthesis method

A technique for the synthesis of Astragalus membranaceus and its synthesis method, which is applied in the field of synthesis of Astragalus membranaceus saponin II, which can solve problems such as the failure of Astragalus saponin and the unreported synthesis of Astragalus membranaceus saponin II, and achieve the promotion of active mechanism research, high efficiency and high efficiency. The effect of stereoselectivity

Active Publication Date: 2017-06-13
JIANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] Therefore, there is no successful report on the synthesis of astragaloside at home and abroad, and there is no report on the synthesis of astragaloside II

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1: Synthesis of Cycloastragenol Derivative 3 Protected by 3-Hydroxy

[0045]

[0046] Under nitrogen protection, cycloastragenol (400mg, 0.82mmol) was dissolved in dry DMF (0.6mL) and TBSCl (489mg, 3.27mmol), imidazole (333mg, 4.90mmol) 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 with 1mol / l HCl, saturated sodium bicarbonate, and saturated NaCl successively, dried over anhydrous sodium sulfate, filtered with suction, concentrated the crude product under reduced pressure, and then the column layer Compound 2 (376.5 mg, 76.8%) was obtained as a white solid: [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),2.00-1.92(m,4H),1.76(dd,J= 4.0,12.0Hz,1H),1.25(s,...

Embodiment 2

[0047] Example 2: Synthesis of Cycloastragenyl Alcohol Derivative 3 Protected by All Hydroxyl Groups

[0048]

[0049] Under nitrogen protection, under the condition of 0 degrees Celsius, compound 2 (133mg, 0.22mmol), PPy (58mg, 0.44mmol) was dissolved in dry toluene (2ml), then acetic anhydride (0.18ml, 2.2mmol) was added to the system, DIPEA (0.479ml, 3.3mmol), the system was slowly raised to room temperature and then heated to 105 degrees Celsius, stirred until TLC tracking showed that the reaction of the raw materials was complete, the reaction system was extracted with ethyl acetate, and successively with 1mol / l HCl, saturated bicarbonate Wash with sodium and saturated NaCl, dry over anhydrous sodium sulfate, filter with suction, concentrate the crude product under reduced pressure, and then column chromatography to obtain compound 3 (139.7 mg, 99%) as a white solid: [α] D 25 =78.3 (c=1, CHCl 3 ); 1 H NMR (400MHz, CDCl 3 )δ5.31(m,1H),4.70(td,J=4.8,8.8Hz,1H),3.96(t,...

Embodiment 3

[0050] Embodiment 3: Synthesis of the cycloastragenol derivative 4 exposed to the 3-hydroxyl group

[0051]

[0052] Under the protection of nitrogen, compound 3 (20mg, 0.03mmol) was dissolved in dry methanol (2mL), and camphorsulfonic acid (26mg, 0.11mmol) was added at room temperature, stirred until TLC tracking showed that the reaction of the raw material was complete, and concentrated under reduced pressure The crude product, followed by column chromatography gave white solid compound 4 (15 mg, 88.9%): [α] D 25 =162.2 (c=1, CHCl 3 ); 1 H NMR (400MHz, CDCl 3)δ5.35-5.30 (m, 1H), 4.76 (td, J = 4.4, 9.2Hz, 1H), 4.02 (t, J = 7.6Hz, 1H), 3.32 (dd, J = 3.6, 10.8Hz, 1H ),2.43(d,J=8.0Hz,1H),2.18-2.12(m,2H),2.01(s,3H),2.00(s,3H),1.97(s,3H),1.43(s,3H) ,1.41(s,3H),1.324(s,3H),1.319(s,3H),0.99(s,3H),0.96(s,3H),0.91(s,3H),0.59(d,J=4.8 Hz,1H),0.36(d,J=4.4Hz,1H); 13 C NMR (100MHz, CDCl 3 )δ170.4, 170.2, 85.5, 83.1, 81.3, 77.8, 75.8, 70.7, 57.5, 49.7, 46.4, 46.3, 45.5, 45.1, 41....

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Abstract

The invention discloses an astramembrannin II synthesis method. The astramembrannin II synthesis method comprises the following steps: (1) selectively protecting 3-hydroxy of cycloastragenol through TBS; (2) protecting 6-hydroxy, 16-hydroxy and 20-hydroxy of cycloastragenol through Ac; (3) selectively removing 3-hydroxy; (4) constructing 3-glucosidic bond; (5) removing all protecting groups in a molecule to obtain astramembrannin II. The method effectively distinguishes the 3-hydroxy in the cycloastragenol, efficiently and highly stereoselectively constructs the 3-glucosidic bond, effectively synthesizes the astramembrannin II, fills the blank of the existing technology, and greatly promotes the progress of medicine development and researches on the activation mechanism of astragaloside compounds.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and more specifically relates to a method for synthesizing astragaloside II. Background technique [0002] Astragalus is an important qi-invigorating drug in traditional Chinese medicine. It has the functions of invigorating qi and raising yang, strengthening the body, detoxifying and discharging pus, restraining and promoting muscle growth, etc. Modern studies have shown that Astragalus has the functions of enhancing immunity, anti-aging, anti-tumor, protecting cardiovascular and cerebrovascular, protecting liver and kidney, etc. It is one of the most widely used Chinese herbal medicines. [0003] 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 membranaceu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J17/00
CPCY02P20/55C07J17/005
Inventor 廖进喜孙建松刘婷
Owner JIANGXI NORMAL UNIV
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