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

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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 protopanaxa

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
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Example Embodiment

[0045] Example 1

[0046] Protopanaxtriol 12-OH is selectively protected by methyl

[0047]

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

[0049] Specific experiment process and data:

[0050] Dissolve protopanaxatriol (477mg, 1.0mmol) in dry THF (5mL), cool the reaction system to 0°C, slowly add LiHMDS (1.2mmol) dropwise to the system, stir at 0°C for 10 minutes and then add MeI (1.2mmol), continue to stir 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 with anhydrous sodium sulfate, filtered and concentrated, and then column chromatography (petroleum ether: ethyl acetate = 2: 1) 417 mg (85%) of compound 2a was obtained. [α] D 25 =+10.2(c 1.0,...

Example Embodiment

[0051] Example 2

[0052] Protopanaxiol 12-OH is selectively protected with benzyl

[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 equivalent of the reagent used is relative It is equivalent to the original ginsengtriol.

[0055] Specific experiment 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) to the system dropwise, stir at 0°C for 10 minutes and then add BnBr (1.2mmol), continue to stir 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 with anhydrous sodium sulfate, filtered and concentrated, and then column chromatography (petroleum ether: ethyl acetate = 2: 1) 510 mg (90%) of compound 2b was obtained. [α] D 25 =+...

Example Embodiment

[0057] Example 3

[0058] Propanaxtriol 12-OH is selectively protected with Piv (pivaloyl) group

[0059]

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

[0061] Specific experiment process and data:

[0062] Dissolve protopanaxatriol (200mg, 0.4mmol) in dry DCM (5mL), cool the reaction system to -5°C, slowly add dry triethylamine (0.4mL) to the system dropwise, and then heat at -5°C PivCl (0.13Ml, 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*30 mL), washed with saturated brine, dried with anhydrous sodium sulfate, filtered and concentrated, and then column chromatography was used to obtain 210 mg (89%) of compound 2c.

[0063] [α] D 25 =+10.2(c1.0, C...

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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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