Synthesis method of ginseng saponin new derivative, product produced by synthesis method and application of ginseng saponin new derivative

Synthesis method of ginseng saponin new derivative, product produced by synthesis method and application of ginseng saponin new derivative

  • CN 105,801,661 A
  • Filed: 04/29/2016
  • Published: 07/27/2016
  • Est. Priority Date: 04/29/2016
  • Status: Active Application
First Claim
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1. a synthetic method for ginsenoside'"'"'s new derivative, is characterized in that:

  • Comprise the following stepsStep one, the 2-deoxy-D-glucose taking 10mmol and 0.69mmol perchloric acid, in temperature beReacting 1.5h~

    3h under conditions of 35 DEG C~

    60 DEG C, follow the tracks of reaction by TLC, reaction uses frozen water after terminatingBath is cooled to room temperature, adds 20mL shrend and goes out, and adds saturated sodium bicarbonate aqueous solution or saturated aqueous sodium carbonate is adjustedJoint pH value, to 7, takes ethyl acetate and carries out three extractions for 15mL/ time, merge the extract of three times, use respectively15mL water and 15mL saturated sodium-chloride water solution washed once, and filter after drying via anhydrous sodium sulfate, are evaporated offSolvent, obtains compounds I;

    Step 2, take compounds I 5mL described in 3mmol~

    15mL dimethylformamide and dissolve, add3.3mmol acetic acid hydrazine, is reacted 0.5h~

    2h under conditions of temperature is 50 DEG C~

    65 DEG C, is followed the tracks of by TLCReaction, after reaction terminates, adds 20mL shrend and goes out, and takes ethyl acetate and carries out three extractions for 15mL/ time, mergesThe extract of three times, washed once, via anhydrous with 15mL water and 15mL saturated sodium-chloride water solution respectivelySodium sulfate filters after drying, and solvent is evaporated off, and pillar layer separation obtains compound ii;

    Step 3, take compound ii 10mL described in 3.1mmol~

    15mL anhydrous methylene chloride and dissolve, add3mL Tritox and the 1 of 0.3mmol, 8-diazabicylo 11 carbon-7-alkene, protect in room temperature and noble gasReacting 2.5h~

    3.5h under conditions of protecting, wherein said noble gas is nitrogen or helium, is followed the tracks of by TLCReaction, reaction terminates rear kieselguhr and filters, reclaims filtrate, and pillar layer separation obtains compound III;

    Step 4, take 2.76mmol compound III and 2.76mmol ginsenoside 10mL~

    15mL dichloromethaneAlkane dissolves, and adds 0.2mmol tert-butyl group dimethyl silyl triflate, at room temperature reaction 1.5h~

    2.5h,Following the tracks of reaction by TLC, reaction terminates rear solvent evaporated, and pillar layer separation obtains compounds Ⅳ

    ,Wherein said ginsenoside be 20 (S)-3 β

    , 12 β

    , 20 beta-triol-24 (25)-alkene-dammarane,20 (R)-3 β

    , 12 β

    , 20 beta-triol-24 (25)-alkene-dammarane,20 (S)-3 β

    , 6 α

    , 12 β

    , 20-tetrol-24 (25)-alkene-dammaraneOr 20 (R)-3 β

    , 6 α

    , 12 β

    , 20-tetrol-24 (25)-alkene-dammarane;

    Step 5, addition 5mL~

    10mL absolute methanol, addition in compounds Ⅳ

    described in 1.42mmol0.19mmol Feldalat NM, at room temperature reaction 0.5h~

    1.5h, follow the tracks of reaction by TLC, after reaction terminates,Addition saturated ammonium chloride regulation pH value is to 7, and solvent evaporated, pillar layer separation obtains ginsenoside'"'"'s new derivative.

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