Large-scale synthesis method of natural alpha-glucosidase inhibitor Penasullate A
A technology of glucosidase and synthesis method, applied in the directions of organic chemistry method, organic chemistry, drug combination, etc., can solve the problem that PenasulfateA cannot be synthesized on a large scale, and achieve the effect of shortening steps and time.
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[0066] In an embodiment of the present application, as figure 1 , Figure 4 and Figure 5 As shown, a large-scale synthesis method of a natural α-glucosidase inhibitor Penasulfate A is provided, the method comprising:
[0067] S1. respectively obtain compound 6, compound 7 and compound 3;
[0068] S2. The compound 6 and the compound 7 are subjected to a Suzuki coupling reaction to obtain the compound 4;
[0069] S3. The compound 4 and the compound 3 are subjected to the first olefin metathesis reaction under the action of the first preset catalyst to obtain the compound 16;
[0070] S4. The compound 16 is subjected to the first hydrogenation reduction reaction to obtain the compound 2;
[0071] S5. obtain the methanol solution of acetyl chloride;
[0072] S6. The methanol solution of the compound 2 and the acetyl chloride is subjected to a deprotection reaction, followed by sulfonation and pH adjustment to obtain a natural α-glucosidase inhibitor Penasulfate A that can be...
Example Embodiment
[0119] Example 1
[0120] like figure 1 , Figure 4 and Figure 5 Shown, a kind of large-scale synthesis method of natural α-glucosidase inhibitor Penasulfate A, described method comprises:
[0121] S1. respectively obtain compound 6, compound 7 and compound 3;
[0122] S2. The compound 6 and the compound 7 are subjected to a Suzuki coupling reaction to obtain the compound 4;
[0123] S3. The compound 4 and the compound 3 are subjected to the first olefin metathesis reaction under the action of the first preset catalyst to obtain the compound 16;
[0124] S4. The compound 16 is subjected to the first hydrogenation reduction reaction to obtain the compound 2;
[0125] S5. obtain the methanol solution of acetyl chloride;
[0126] S6. The methanol solution of the compound 2 and the acetyl chloride is subjected to a deprotection reaction, followed by sulfonation and pH adjustment to obtain a natural α-glucosidase inhibitor Penasulfate A that can be produced on a large scale;...
Example Embodiment
[0164] Example 2
[0165] Comparing Embodiment 2 and Embodiment 1, the difference between Embodiment 2 and Embodiment 1 is:
[0166] The oxidant used in the oxidation reaction includes sodium chlorite, tetramethylpiperidine oxide and sodium hypochlorite. The equivalent of sodium chlorite is 2 times that of compound 10, and the equivalent of tetramethylpiperidine oxide is 0.05 times that of compound 10. Sodium hypochlorite The equivalent of compound 10 is 0.02 times.
[0167] The reaction temperature for the Suzuki coupling reaction was 25°C.
[0168] The first preset catalyst was the Hoveyda-Grubbs II catalyst.
[0169] The reaction temperature of the first olefin metathesis reaction is 45°C, and the solvent used in the first olefin metathesis reaction is 1,2-dichloroethane or toluene.
[0170] The reaction time of the first hydrogenation reduction reaction is 0.5h; the mass fraction of Pd / C catalyst is 5%.
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