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A preparation method of fumagillin amino alcohol

A technology of fumagillin amino alcohol and fumagillin, which is applied in the field of preparation of fumagillin amino alcohol, can solve the problem of fish endangering fish health and freshwater aquaculture, and affecting beekeeping and agricultural production activities impact and other issues, to achieve the effect of reducing the steps of separation and purification, low toxicity and high synthesis efficiency

Inactive Publication Date: 2019-06-11
INST OF QUALITY STANDARD & TESTING TECH FOR AGRO PROD OF CAAS
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example, the harmful effect of microsporidiosis on bees not only seriously affects beekeeping, but also has an impact on crop pollination and even the entire agricultural production activities; at the same time, its impact on fish has seriously endangered the health of fish and freshwater aquaculture

Method used

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  • A preparation method of fumagillin amino alcohol
  • A preparation method of fumagillin amino alcohol
  • A preparation method of fumagillin amino alcohol

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Experimental program
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Embodiment 1

[0020] Embodiment 1, fumagillin amino alcohol shown in synthetic formula I

[0021]

[0022] The reaction process is as follows:

[0023] (1) Synthesis of compound shown in formula III

[0024] Dissolve L-lysine (1.0mmol) represented by formula II in methanol (10ml) at 0°C, gradually add thionyl chloride (2.0mmol) dropwise, keep the temperature for 30min, then warm up to room temperature, keep stirring for 24h . Potassium borohydride (3.0 mmol) was added, and stirring was continued at room temperature for 24 h. After completion of the reaction, wash the water phase with ethyl acetate, keep the water phase, adjust the pH value of the water phase to alkaline (pH>10), then add ethyl acetate and wash the water phase 3 times with a separatory funnel, Add anhydrous magnesium sulfate for drying, and concentrate using a rotary evaporator to obtain a crude sample. Finally, it was placed in a ventilated place and dried to obtain the compound shown in formula III with a yield of 7...

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Abstract

The invention discloses a preparation method of fumagillin amino alcohol shown as a formula I in the specification. The method comprises the following steps: (1) reducing amino acid shown in a formulaII to obtain a compound shown in a formula III; and (2) under the heating condition of a methanol solution, carrying out an ammonium salt synthesis reaction on fumagillin and the compound shown in the formula III to obtain fumagillin amino alcohol. The preparation method is short in reaction route and high in synthesis efficiency, the separation and purification steps are reduced, and mass production can be achieved. Meanwhile, the synthesized fumagillin amino alcohol is low in toxicity, can be dissolved and degraded in nature and is good in water solubility.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of fumagillin amino alcohol. Background technique [0002] Fumagillin is an antibiotic drug mainly used to treat microsporidiosis. Microsporidiosis mainly parasitizes in the epithelial cells of the digestive tract of insects and the skin and muscles of fish, and is also found in annelids and some other invertebrates. The impact of crops on microsporidiosis cannot be ignored. For example, the harmful effect of microsporidiosis on bees not only seriously affects beekeeping, but also has an impact on crop pollination and even the entire agricultural production activities; at the same time, its impact on fish has seriously endangered the health of fish and freshwater aquaculture . Judging from the effect of preventing and treating microsporidiosis abroad, fumagillins are the best choice to replace antifungal drugs such as metronidazole. In recent ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D301/00C07D303/22C07C213/02C07C215/18
Inventor 王敏王彤彤常白杨汤晓艳周剑杨梦瑞
Owner INST OF QUALITY STANDARD & TESTING TECH FOR AGRO PROD OF CAAS
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