A kind of synthetic method of 25-o-glucosyl cycloastragenol

A cyclo-astragalus and glucose-based technology is applied in the field of preparation of 25-O-glucosyl cyclo-astragalus, which can solve the problems of unsuccessful synthesis of astragaloside, no reports of synthesis of astragalus, etc., and achieves the advancement of active mechanism research and improvement. The effect of its drug development process

Active Publication Date: 2018-11-09
JIANGXI NORMAL UNIV
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  • Abstract
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AI Technical Summary

Problems solved by technology

[0009] Therefore astragaloside synthesis has no successful reports at home and abroad so far, and the synthesis of 25-O-glucosyl cycloastragenol has not been reported yet.

Method used

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  • A kind of synthetic method of 25-o-glucosyl cycloastragenol
  • A kind of synthetic method of 25-o-glucosyl cycloastragenol
  • A kind of synthetic method of 25-o-glucosyl cycloastragenol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1: Selective hydroxyl protection of cycloastragenol: Compound 2 was obtained;

[0046]

[0047] Under nitrogen protection, at 0°C, cycloastragenol (180mg, 0.37mmol), PPy (108mg, 0.74mmol) was dissolved in dry toluene (10mL), and acetic anhydride (348μL, 3.67mmol) was added to the system, DIPEA (912 μL, 5.55 mmol), the system was slowly raised to room temperature and then heated to 105 ° C, 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 sodium bicarbonate , washed with saturated NaCl, dried over anhydrous sodium sulfate, filtered with suction, concentrated the crude product under reduced pressure, and then obtained white solid compound 2 (184mg, 81.3%) by column chromatography: [α] D 25 =73.5 (c=1, CHCl 3 ); 1 H NMR (400MHz, CDCl 3 )δ5.44-5.39(m,1H),4.75(td,J=4.4,9.2Hz,1H),4.60(dd,J=4.4,11.2Hz,1H),3.72(dd,J=6.8,8.4Hz ,1...

Embodiment 2

[0048] Example 2: Glycosidation reaction to obtain compound 4;

[0049]

[0050] Under nitrogen protection, compound 2 (12 mg, 0.02 mmol) and glucosynyl ester donor 3 (31 mg, 0.05 mmol) were dissolved in dry dichloromethane (2 mL), and 4A molecular sieves (2 mg) were added, at room temperature Stir for half an hour before adding the catalyst Ph 3 PAuNTf2 (0.002mmol), continued to stir at room temperature until TLC tracking showed that the reaction of raw materials was complete, the crude product was concentrated under reduced pressure, and then column chromatography gave white solid compound 4 (22mg, 94.42%): [α] D 25 =72.6 (c=1, CHCl 3 ); 1 HNMR (400MHz, CDCl 3 )δ8.00-7.95(m,4H),7.91(dd,J=1.2,8.4Hz,2H),7.85(dd,J=1.2,8.0Hz,2H),7.56-7.48(m,3H),7.44 -7.33(m,7H),7.30-7.27(m,2H),5.92(t,J=9.6Hz,1H),5.58(t,J=10.0Hz,1H),5.50(dd,J=8.0,10.0 Hz, 1H), 5.29-5.26(m, 1H), 5.20(d, J=8.0Hz, 1H), 4.74(td, J=4.0, 9.2Hz, 1H), 4.60-4.56(m, 2H), 4.47 (dd, J=6.8, 12.0Hz, 1H), 4.16-4.11(m,...

Embodiment 3

[0051] Example 3: Final deprotection reaction: 25-O-glucosyl cycloastragenol I was obtained;

[0052]

[0053] Under the protection of nitrogen, compound 4 (20mg, 0.017mmol) was dissolved in dry methanol (2mL), then sodium methoxide (0.17mmol) was added, and stirred at room temperature until TLC tracking showed that the reaction of the raw material was complete, and then neutralized with an acidic resin PH to neutral and slightly acidic, suction filtered, concentrated the crude product under reduced pressure, and then column chromatography to obtain the white solid compound 25-O-glucosyl cycloastragenol I (9.2mg, 84%): [α] D 25 =21.4 (c=1, CHCl 3 ); 1 H NMR (400MHz, C 5 D. 5 N)δ5.10(d,J=8.0Hz,1H),4.95-4.88(m,2H),4.47(dd,J=2.8,11.6Hz,1H),4.34(dd,J=4.8,11.6Hz, 1H), 4.25-4.16(m, 2H), 4.09(dd, J=9.2, 16.0Hz, 1H), 3.93-3.89(m, 2H), 3.83-3.77(td, J=4.4, 10.0Hz, 1H) ,3.70(dd,J=4.4,11.2Hz,1H),2.87-2.80(m,1H),2.47(d,J=7.6Hz,1H),1.92(s,3H),1.68(s,3H), 1.43(s,3H),1.38(s,6H),1.3...

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Abstract

The invention discloses a method for synthesizing 25-O-glucosyl cycloastragenol, under the action of PPy, acid anhydride and DIPEA, cycloastragenol is selectively protected at 3-position, 6-position and 16-position at 100-120°C OH; under the action of a catalyst, a glycosidation reaction occurs, and finally all protecting groups are removed to obtain 25‑O‑glucosyl cycloastragenol. The present invention prepares 25-O-glucosyl cycloastragenol with high efficiency, high stereoselectivity and high yield, fills the gap 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 25-O-glucosyl cycloastragenol. 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 astragalosides have shown promising medicinal prospects in terms of immune regulation, hypoglycemia, insulin resistance improvement, antitumor, cardiovascular system regulation, antiviral, and antioxidant activities. [0003] Although the wide application prospects of astragalosides have prompted people to cont...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J53/00
CPCY02P20/55
Inventor 廖进喜孙建松刘婷
Owner JIANGXI NORMAL UNIV
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