Synthesis method and application of gastrodin semihydrate
A synthesis method and hemihydrate technology, which are applied in the directions of organic chemistry methods, chemical instruments and methods, sugar derivatives, etc., can solve problems such as being unfavorable to industrialized production, generating heavy metals, prolonging reaction routes, etc., and achieving a simple and easy operation method. The effect of simple operation, low cost and reasonable synthesis route
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Embodiment 1
[0039] This example provides the preparation of an intermediate 2-bromo-α-D-glucose tetraacetate, and its synthetic route is as follows:
[0040]
[0041] Specific steps include:
[0042] Add 100.0g of β-D-glucose pentaacetate into 400ml of dichloromethane, and lower the temperature to below 5°C;
[0043] Control the temperature not to exceed 5°C, add 125.6g of 33% acetic acid hydrobromide dropwise, raise the temperature to 15-25°C and stir for 6 hours.
[0044] After the complete reaction of the raw material SM1 was monitored by TLC, the reaction solution was added to 800 mL of saturated aqueous sodium bicarbonate solution at 5° C., stirred for 10 min, and separated.
[0045] The aqueous phase was extracted once with 400 ml of DCM, and the combined organic phases were washed with 400 ml of aqueous solution.
[0046] The organic phase was dried with 40 g of anhydrous sodium sulfate, filtered, and the filtrate was distilled under reduced pressure to obtain a light yellow tra...
Embodiment 2
[0049] This example provides the preparation of an intermediate 2-bromo-α-D-glucose tetraacetate, and its synthetic route is as follows:
[0050]
[0051] Specific steps are as follows:
[0052] Add 100.0g of β-D-glucose pentaacetate into 300ml of tetrahydrofuran, and lower the temperature to below 5°C;
[0053] Control the temperature not to exceed 5°C, add 94.2g of 33% hydrobromic acetic acid dropwise, and after the drop is complete, raise the temperature to 25-35°C and stir for 4 hours.
[0054] After the complete reaction of raw material SM1 was monitored by TLC, the reaction solution was added to 800 mL of 5% sodium carbonate aqueous solution at 5°C, stirred for 10 min, a large amount of white solid was precipitated, filtered with suction, and the filter cake was washed with water.
[0055] Add 100 mL of methanol to the filter cake, stir at room temperature for 30 min, filter, wash the filter cake with 100 ml of n-heptane, and dry the filter cake under reduced pressur...
Embodiment 3
[0057] This example provides the preparation of an intermediate 2-bromo-α-D-glucose tetraacetate, and its synthetic route is as follows:
[0058]
[0059] Specific steps are as follows:
[0060] Add 100.0g of β-D-glucose pentaacetate into 500ml of ethanol and cool down to below 5°C;
[0061] Control the temperature not to exceed 5°C, add 198.4g of 33% acetic acid hydrobromide dropwise, raise the temperature to 35-45°C and stir for 2 hours.
[0062] After the complete reaction of raw material SM1 was monitored by TLC, the reaction solution was added to 1000 mL of 5% potassium carbonate aqueous solution at 5°C, stirred for 10 min, a large amount of white solid was precipitated, filtered with suction, and the filter cake was washed with water.
[0063] Add 150 mL of isopropanol to the filter cake, stir at room temperature for 30 min, filter, wash the filter cake with 100 ml of n-hexane, and dry the filter cake under reduced pressure at 20°C for 3 h to obtain 96.8 g of white s...
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