A gastrodin compound, its preparation method and application
A compound, gastrodin technology, applied in the preparation of sugar derivatives, chemical instruments and methods, organic chemistry, etc., can solve problems such as performance needs to be improved
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[0034] The present invention also provides a preparation method of gastrodin compounds, comprising:
[0035] S1) reacting the compound represented by formula (II) with a hydroxyl protecting reagent or a halogenating reagent to obtain an intermediate product;
[0036] S2) reacting the intermediate product with a compound represented by formula (II) to obtain a compound represented by formula (III);
[0037] S3) deprotecting the compound represented by the formula (III) to obtain a gastrodin compound represented by the formula (I);
[0038]
[0039] The compound represented by the formula (II) is reacted with a hydroxyl protecting reagent or a halogenating reagent to obtain an intermediate product; by reacting with a hydroxyl protecting reagent or a halogenating reagent, the alcoholic hydroxyl group can be converted into an easily leaving group. The hydroxyl protection reagent is preferably MsCl, TsCl, AcO 2 With one or more in TFAA; The halogenation reagent is preferably P...
Embodiment 1
[0052] About 25L of the mother liquor produced in the refining process of gastrodin production was collected, concentrated to remove the solvent, and the obtained solid sample was refined again according to the operation of the refining process, and the mother liquor was further concentrated and enriched four times to obtain a sample with relatively high compound content. The sample was determined according to the chromatographic conditions for the inspection of related substances in gastrodin injection, and there was [M+Na] in MS + For 577 and [2M+Na] + The molecular ion peak is 1131, and the molecular weight of the dimer is estimated to be 534. Further, the new compound is determined by high-resolution mass spectrometry, and the MS has [M+Na] + is 577.1904, the molecular formula is C 26 h 34 NaO 13 .
[0053] The above samples were separated by preparative high-performance liquid chromatography (chromatographic conditions: YMC-ActusTriart C18 (150mm×30mm, 5 μm) chromatog...
Embodiment 2
[0056] Embodiment 2: the synthesis of intermediate product
[0057]
[0058] Dissolve 10.00g of acetylgastrodin in 100mL of dichloromethane, add 6.12mL of triethylamine, cool down to -20°C, add 2.57mL of MsCl dropwise, after the dropwise addition, slowly raise the temperature to 0°C and stir for 1h, TLC shows that the reaction is complete ; Add saturated NH to the reaction solution 4 Cl solution was extracted, dichloromethane was extracted three times, the organic layers were combined, anhydrous Na 2 SO 4 Dry, spin dry under pressure, and crystallize to obtain 10.71 g of white solid, yield: 91.3%. MS(ESI)m / z:546[M+Na] + .
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