Synthesizing process of beta-cyclodextrin derivative

Abstract

The invention relates to a synthesizing process of a beta-cyclodextrin derivative. The synthesizing process includes: in the presence of barium carbonate, using tetrahydrofuran as the solvent to allowbeta-cyclodextrin to have reaction with dimethyl carbonate at the temperature of 10-60 DEG C and normal pressure for 0.5-48 hours, wherein the mole ratio of the beta-cyclodextrin to dimethyl carbonate is 1:0.1-1:9, the mass ratio of the tetrahydrofuran to the beta-cyclodextrin is 2:1-1500:1, and the weight ratio of barium carbonate to the beta-cyclodextrin is (0.25-2):1; filtering to remove the barium carbonate and insoluble matter, and performing reduced pressure distillation to remove the solvent to obtain intermediate product 2-O-methyl-beta-cyclodextrin; dissolving the intermediate product into a strong alkaline solution, and dropwise adding epoxy propane and anhydrous ethanol to perform reaction at the temperature of 0-70 DEG C and normal pressure for 0.5-56 hours; using a sulfuric acid solution to neutralize the strong alkaline solution until the strong alkaline solution is neutral, and distilling to obtain white solid; dissolving the white solid with tetrahydrofuran, filteringto remove sulfate, and distilling to remove the tetrahydrofuran to obtain 2-O-methyl-6-O-(2-hydroxypropyl)-beta-cyclodextrin. The 2-O-methyl-6-O-(2-hydroxypropyl)-beta-cyclodextrin has large application potential in fields such as medicine auxiliaries, food additives and chemistry and chemical engineering, and the synthesizing process is green and simple in synthesizing route and mild in reactioncondition.

Description

technical field [0001] The invention relates to a synthesis process of a beta-cyclodextrin derivative, which is a newly synthesized compound. It specifically relates to a method of using green methylating reagent dimethyl carbonate to replace the hydrogen atom on the 2-hydroxyl group of β-cyclodextrin to synthesize 2-O-methyl-β-cyclodextrin; Synthesis of 2-O-methyl-6-O-(2-hydroxypropyl)-β-cyclodextrin by ring-opening reaction with the hydroxyl group at the 6-position of 2-O-methyl-β-cyclodextrin under conditions The synthesis process of β-cyclodextrin derivatives, the synthesized compounds have great application potential in the fields of pharmaceutical excipients, food additives, chemical engineering, etc. The synthesis route is green, simple, and the reaction conditions are mild. Background technique [0002] β-cyclodextrin is a kind of cylindrical compound formed by α-1,4 glycosidic linkages of 7 glucose monomers. Because β-cyclodextrin has a cavity molecular structure ...

AI Technical Summary

Problems solved by technology

Both methyl-β-cyclodextrin and (2-hydroxypropyl)-β-cyclodextrin have their own advantages in properties, but also have their own disadvantages: the solubility of methylated-β-cyclodextrin It decreases sharply with the increase of temperature, which may cause drug precipitation or other adverse effects during use; (2-hydroxypropyl)-β-cyclodextrin needs to be improved in terms of drug bioavailability

Through a large number of experiments, it is found that the use of N, N-dimethylformamide solvent is unscientific, not energy-saving, and not practical. It is urgent to find a more reliable and lower-cost raw material for large-scale production

[0005] 2. In the experiment, it was found that at a temperature of 10-60°C, the catalytic effect of anhydrous potassium carbonate on the reaction of β-cyclodextrin and dimethyl carbonate was not good, which was not conducive to the progress of the reaction, resulting in slow reaction and poor activity.

[0006] 3. The invention patent does not determine the specific substitution position of the methyl group

[0008] However, the 2-O-methyl-6-O-(2-hydroxypropyl)-β-cyclodextrin applied for in the present invention is a new compound, and all documents: patents, journal papers, conference papers, dissertations, etc. New compounds that have not been reported in the literature

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