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Synthesis method for 20-bit sugar connected protopanaxatriol analog ginsenoside and analog

A technology of protopanaxatriol and its synthesis method, which is applied in the field of preparation of protopanaxatriol ginsenoside F1 and its analogues, and can solve the problems of difficult acquisition, high price of enzymes, difficulty in providing ginsenoside samples, etc.

Active Publication Date: 2012-02-01
SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

((a) Danieli, B.; Falcone, L.; Monti, D.; Riva, S.; Gebhardt, S.; Schubert-Zsilavecz, M.J. Org. Chem. 2001, 66, 262. .-R.; Choi, K.-J.; Suzuki, K.; Suzuki, Y.Chem.Pharm.Bull.2003, 51, 404.) Although this method has been applied to protopanaxatriol ginsenosides However, in view of the high price of enzymes and the disadvantages of not being easy to obtain, it is difficult to provide a large number of ginsenoside samples that can be used for activity testing and mechanism research.

Method used

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  • Synthesis method for 20-bit sugar connected protopanaxatriol analog ginsenoside and analog
  • Synthesis method for 20-bit sugar connected protopanaxatriol analog ginsenoside and analog
  • Synthesis method for 20-bit sugar connected protopanaxatriol analog ginsenoside and analog

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Selective Protection of Protopanaxatriol 12-OH Using Methyl

[0047]

[0048] Reagents and conditions: a) MeI (1.2 equiv.), LiHMDS (1.2 equiv.), THF, 0°C. Wherein LiHMDS is lithium hexamethyldisilazide; THF is tetrahydrofuran; the equivalents of the reagents used are relative to the original ginseng three Alcohol equivalent.

[0049] Specific experimental process and data:

[0050] Dissolve protopanaxatriol (477mg, 1.0mmol) in dry THF (5mL), cool the reaction system to 0°C and slowly add LiHMDS (1.2mmol) dropwise to the system, stir at 0°C for 10 minutes and then add MeI (1.2 mmol), stirring was continued for 2 hours. The reaction was quenched with saturated ammonium chloride, extracted with a large amount of ethyl acetate, washed with water (3*30mL), washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated, followed by column chromatography (petroleum ether: ethyl acetate = 2: 1) Obtain 417 mg (85%) of compound 2a. [α] D 25 =...

Embodiment 2

[0052] Selective protection of protopanaxatriol 12-OH by benzyl group

[0053]

[0054] Reagents and conditions: a) BnBr (1.2equiv.), LDA (1.2equiv.), THF, 0°C. Wherein BnBr is benzyl bromide; LDA is lithium diisopropylamide; THF is tetrahydrofuran; the reagent equivalents used are relative Equivalent to protopanaxatriol.

[0055] Specific experimental process and data:

[0056] Dissolve protopanaxatriol (477mg, 1.0mmol) in dry THF (5mL), cool the reaction system to 0°C, slowly add LDA (1.2mmol) dropwise to the system, stir at 0°C for 10 minutes, then add BnBr (1.2 mmol), stirring was continued for 2 hours. The reaction was quenched with saturated ammonium chloride, extracted with a large amount of ethyl acetate, washed with water (3*30mL), washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated, followed by column chromatography (petroleum ether: ethyl acetate = 2: 1) Obtain 510 mg (90%) of compound 2b. [α] D 25 =+15.0 (c 1.0, CHCl...

Embodiment 3

[0058] Selective Protection of Protopanaxatriol 12-OH Using Piv(pivaloyl) Group

[0059]

[0060] Reagents and conditions: a) PivCl (1.2 equiv.), Et 3 N, DCM, -5°C. Wherein PivCl is pivaloyl chloride; DCM is dichloromethane; the equivalents of the reagents used are equivalents relative to protopanaxatriol.

[0061] Specific experimental process and data:

[0062] Protopanaxatriol (200mg, 0.4mmol) was dissolved in dry DCM (5mL), the reaction system was cooled to -5°C, and dry triethylamine (0.4mL) was slowly added dropwise to the system, then at -5°C PivCl (0.13 Ml, 1.2 equiv.) was added dropwise to the reaction system, and stirring was continued for 1.5 hours. The reaction was quenched with saturated ammonium chloride, extracted with a large amount of ethyl acetate, washed with water (3*30mL), washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated, and column chromatography gave 210 mg (89%) of compound 2c.

[0063] [α] D 25 =+10.2(...

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Abstract

The invention discloses a preparation method of 20-bit sugar connected protopanaxatriol protopanaxatriol analog ginsenoside, which comprises the following steps of: (1) introducing protopanaxatriol 12-bit hydroxyl protecting groups; (2) introducing protopanaxatriol 3, 6-bit protecting groups; (3) introducing 20-bit hydroxyl sugar groups; and (4) removing protecting groups. No report about the 20-bit sugar connected protopanaxatriol protopanaxatriol analog ginsenoside synthesis is reported in the prior art. The invention provides the efficient and applicable synthesis method.

Description

technical field [0001] The invention relates to a preparation method of protopanaxatriol ginsenoside F1 and analogues connected with sugar at the 20-position. Background technique [0002] Ginseng is the general name of 14 species of Araliaceae (Araliaceae) plants of the genus Panax. The ginseng used in traditional Chinese medicine is Asian ginseng (P.ginseng). Human physique, prolong life. Not only that, but the efficacy of ginseng in the central nervous system, cardiovascular and cerebrovascular, endocrine and human immune systems has gradually been recognized by people. With the development of modern means of separation and identification, it becomes possible to determine the target of active ingredients in ginseng. Saponins, polysaccharides, peptides, polyacetylene alcohol fatty acids, etc. have been isolated from ginseng (Lee, F. Facts about Ginseng, the Elixir of Life. Hollyn International Corp., Elizabeth, NJ, 1992). So which ingredient plays a key role in the biol...

Claims

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Application Information

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IPC IPC(8): C07J17/00C07J75/00
CPCY02P20/55
Inventor 俞飚孙建松牛一鸣廖进喜
Owner SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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