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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.

Pending Publication Date: 2022-05-03
JIANGHAN UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] This application provides a large-scale synthesis method of the natural α-glucosidase inhibitor Penasulfate A, to solve the technical problem that the α-glucosidase inhibitor Penasulfate A in the prior art cannot be synthesized on a large scale in the industry

Method used

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  • Large-scale synthesis method of natural alpha-glucosidase inhibitor Penasullate A
  • Large-scale synthesis method of natural alpha-glucosidase inhibitor Penasullate A
  • Large-scale synthesis method of natural alpha-glucosidase inhibitor Penasullate A

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preparation example Construction

[0066] In one embodiment of this application, as figure 1 , Figure 4 and Figure 5 Shown, provide a kind of large-scale synthetic method of natural α-glucosidase inhibitor Penasulfate A, described method comprises:

[0067] S1. Obtain compound 6, compound 7 and compound 3 respectively;

[0068] S2. The compound 6 and compound 7 were subjected to Suzuki coupling reaction to obtain compound 4;

[0069] S3. performing the first olefin metathesis reaction on the compound 4 and the compound 3 under the action of the first predetermined catalyst to obtain the compound 16;

[0070] S4. Carrying out the first hydrogenation reduction reaction of the compound 16 to obtain the compound 2;

[0071] S5. obtain the methanol solution of acetyl chloride;

[0072] S6. Deprotecting the compound 2 and the methanol solution of acetyl chloride, followed by sulfonation and pH adjustment, to obtain Penasulfate A, a natural α-glucosidase inhibitor that can be produced on a large scale;

[0073...

Embodiment 1

[0120] Such as figure 1 , Figure 4 and Figure 5 Shown, a kind of large-scale synthetic method of natural α-glucosidase inhibitor Penasulfate A, described method comprises:

[0121] S1. Obtain compound 6, compound 7 and compound 3 respectively;

[0122] S2. The compound 6 and compound 7 were subjected to Suzuki coupling reaction to obtain compound 4;

[0123] S3. performing the first olefin metathesis reaction on the compound 4 and the compound 3 under the action of the first predetermined catalyst to obtain the compound 16;

[0124] S4. Carrying out the first hydrogenation reduction reaction of the compound 16 to obtain the compound 2;

[0125] S5. obtain the methanol solution of acetyl chloride;

[0126] S6. Deprotecting the compound 2 and the methanol solution of acetyl chloride, followed by sulfonation and pH adjustment, to obtain Penasulfate A, a natural α-glucosidase inhibitor that can be produced on a large scale;

[0127] Wherein, the general structural formula of...

Embodiment 2

[0165] Compare embodiment 2 and embodiment 1, the difference of embodiment 2 and embodiment 1 is:

[0166] The used oxidizing agent of oxidation reaction comprises sodium chlorite, tetramethyl piperidine oxide and sodium hypochlorite, and the equivalent of sodium chlorite is 2 times of compound 10, and the equivalent of tetramethyl piperidine oxide is 0.05 times of compound 10, and sodium hypochlorite The equivalent of is 0.02 times that of compound 10.

[0167] The reaction temperature of the Suzuki coupling reaction was 25 °C.

[0168] The first preset catalyst is 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 0.5 h; the mass fraction of the Pd / C catalyst is 5%.

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Abstract

The invention relates to the technical field of biological medicines, in particular to a large-scale synthesis method of a natural alpha-glucosidase inhibitor Penasullate A. The method comprises the following steps: respectively obtaining a compound 6, a compound 7 and a compound 3; carrying out Suzuki coupling reaction on the compound 6 and the compound 7 to obtain a compound 4; performing a first olefin metathesis reaction on the compound 4 and the compound 3 under the action of a first preset catalyst to obtain a compound 16; performing a first hydrogenation reduction reaction on the compound 16 to obtain a compound 2; a methanol solution of acetyl chloride is obtained; and carrying out deprotection reaction on the compound 2 and the methanol solution of acetyl chloride, and then carrying out sulfonylation and pH regulation to obtain the natural alpha-glucosidase inhibitor Penasullate A which can be prepared on a large scale. The technical route only needs ten steps, the steps and time required by the reaction are greatly shortened, and large-scale preparation of Penasullate A can be realized.

Description

technical field [0001] The present application relates to the technical field of biomedicine, in particular to a large-scale synthesis method of natural α-glucosidase inhibitor Penasulfate A. Background technique [0002] α-glucosidase is an enzyme that catalyzes the release of glucose by catalyzing the α-glucosidic bond of oligosaccharides or glycoconjugates. It participates in various biochemical functions, such as carbohydrate digestion, glycoprotein processing, etc. Therefore, This makes α-glucosidase an important target for disease treatment, and α-glucosidase inhibitors have broad application prospects in the field of medicine; among the existing drugs for the clinical treatment of type II diabetes, acarbose, migraine Litrol, vogliebol, are better α-glucosidase inhibitors. [0003] Penasulfate A is an open-chain structure disulfate compound containing pipecolinic acid, and its IC for yeast α-glucosidase 50 The value is 4.4μM, which is a new type of α-glucosidase inhi...

Claims

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Application Information

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IPC IPC(8): C07D211/60A61P3/10
CPCC07D211/60A61P3/10C07B2200/07Y02P20/55
Inventor 高阳光邓昌选杨杰鲁望婷
Owner JIANGHAN UNIVERSITY
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