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A synthesis method and technology of alkenose, applied in the direction of organic chemistry, etc., to achieve the effects of high yield, high product purity and fixed reaction time
Active Publication Date: 2012-02-08
JINAN SHENGQUAN GROUP SHARE HLDG
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[0007] These methods will produce impurities during the reaction process, so that the purity of the obtained vinyl sugars is not very high, which will affect the product quality and cause certain restrictions on use; and the reaction speed etc. are not easy to control, which may cause incomplete reaction and waste of raw materials, etc.
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Embodiment 1
[0028] Synthetic method of diacetyl ribosene:
[0029] (1) Take 1000ml of dry and clean one-mouth bottle, add 150g of dichloromethane, and then add 100g of pure triacetyl ribose bromide to dissolve triacetyl ribose bromide to form a solution, and cool to below 10 degrees;
[0030] (2) Take 1000ml of dry and clean three-neck round-bottom flask, install a stirring and condenser, then add 150g of dichloromethane, 50g of zinc powder and 100g of 25wt% ammonium chloride aqueous solution, and mix well;
[0031] (3) Then start the stirring of the three-necked round-bottom flask, the rotating speed is 100r / min, heat the mixture to reflux, stop heating, and start adding the solution prepared in step (1) in batches, adding 20% of the mass of the bromide solution each time One-third, after each addition, due to the exothermic reaction, reflux will occur in the flask. When the reflux phenomenon stops, add the solution again. After all the solution is added, the reflux stops, and the enti...
Embodiment 2
[0035] Synthetic method of diacetyl ribosene:
[0036] (1) Take a 1000ml dry and clean one-mouth bottle, add 150g of dichloromethane, and then add 100g of triacetyl ribose bromide to dissolve the triacetyl ribose bromide to form a solution, and cool to below 10°C;
[0037] (2) Take 1000ml of dry and clean three-necked round-bottom flask, install a stirring and condenser, then add 150g of dichloromethane, 50g of zinc powder and 100g of 30wt% ammonium chloride aqueous solution, and mix well;
[0038] (3) Then start the stirring of the three-necked round-bottom flask, the rotating speed is 100r / min, heat the mixture to reflux, stop heating, and start adding the solution prepared in step (1) in batches, adding 20% of the mass of the bromide solution each time One-third, after each addition, due to the exothermic reaction, reflux will occur in the flask. When the reflux phenomenon stops, add the solution again. After all the solution is added, the reflux stops, and the entire syn...
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Abstract
Relating to the technical field of organic synthesis of glycal, the invention specifically relates to a synthesis method of glycal. The method comprises the steps of: dissolving 100 parts of triacetylribose halide in 150 parts of dichloromethane so as to obtain a halogenated sugar solution which is then cooled to a temperature below 10DEG C; mixing 150 parts of dichloromethane, 50 parts of zinc powder, and 100 parts of an ammonium chloride water solution well in a reaction vessel equipped with a condenser; heating the reaction vessel till generating backflow, then stopping heating, adding thehalogenated sugar solution for several times into the reaction vessel at a speed of 100r / min, with the halogenated sugar solution added of 1 / 20 of the halide solution by mass each time and the backflow generated each time after the adding of the halogenated sugar solution, and adding the halogenated sugar solution again after the end of the backflow, then waiting for the stop of the backflow, thus coming to the end of the reaction. The synthesis method provided in the invention has the advantages of simple operation, easily controllable reaction speed, fixed reaction time, strong repetitive operationality, and convenient product quality control. And the reaction method has high yield and can produce products of high purity.
Description
technical field [0001] The invention relates to the technical field of organic synthesis of vinyl sugars, in particular to a method for synthesizing acylated vinyl sugars. Background technique [0002] In organic synthesis, vinyl sugars and acetylated vinyl sugars are very important raw materials. Acetylated vinyl sugars are usually obtained by reacting zinc and acetic acid with acylated sugar-based halides. This reduction method is a classic method. The C-1 carbocation is then reduced with a metal, and an elimination reaction occurs, but it does not necessarily have to go through the intermediate of the organometallic compound. Using this reaction, Fischer's lab synthesized, for the first time, 3,4,6-tri-O-acetyl-D-glucal from tetraacetylglucose bromide with zinc and acetic acid. [0003] There is also an improved method, which can start from unprotected sugar and perform acetylation, bromination, and elimination reactions in one pot, such as the preparation method discl...
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