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Milbemycin oxime compound and preparation method thereof

A technology of milbexime and compounds, which is applied in the field of milbexime compounds and their preparation, can solve the problems that no one has tried, and achieve the effects of simple operation, low synthesis cost and high yield

Inactive Publication Date: 2014-07-02
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, milbemycin analogues are basically chemically synthesized from milbemycin, and many parasites have developed certain drug resistance to abamectin, milbemycin and milbemycin. Abamectin B1a has not been tried to chemically synthesize milbexime analogs, so it is of great significance to find new cheap and easy-to-obtain antiparasitic drugs in agricultural and animal husbandry production

Method used

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  • Milbemycin oxime compound and preparation method thereof
  • Milbemycin oxime compound and preparation method thereof
  • Milbemycin oxime compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: the preparation of compound 1

[0032] First, 2.35 mL of concentrated H 2 SO 4 and 2.31mL H 2 O mixed, added to 8.5mL of THF, mixed to form H 2 SO 4 / H 2 O / THF mixture. 222mg (0.25mmol) Abamectin B1a was added to a single-necked round bottom flask, and 10mL THF was added under argon protection to dissolve Abamectin B1a, then the flask was placed in an ice bath, and the prepared H 2 SO 4 / H 2 Slowly add the O / THF mixture into the THF solution of abamectin B1a. After the addition is complete, place it in an environment of 18°C ​​for 24 hours. Monitor the progress of the reaction with thin-layer chromatography (TLC). After the reaction is complete, stir 15 mL of ice water was added to the reaction liquid under the conditions, and then extracted three times with dichloromethane (DCM), and the combined organic phase was washed with saturated 3 The solution and water were washed three times respectively, dried, spin-dried, and separated by a silica gel...

Embodiment 2

[0036] Embodiment 2: the preparation of compound 2

[0037] 25mg (0.043mmol) Compound 1 obtained in Example 1 was added to a 25mL single-necked round bottom flask, then 8mL of redistilled DCM was added for dissolution, and 27.6mg (3eq) of pyridinium chlorochromate (PCC ), mixed evenly to form a reaction solution, and stirred at room temperature for 6 h. The progress of the reaction was monitored by TLC. After the reaction was complete, 7 mL of water was added to the reaction solution, extracted three times with DCM, and the combined organic phase was washed three times with saturated brine / water (1 / 1, v / v), dried, spin-dried, and passed through silica gel. The target compound 2 was obtained by column separation with a yield of 91%.

[0038] The structure determination data of compound 2 are as follows:

[0039] 1 H NMR (400MHz, CDCl 3 ):δ6.56(s,1H),6.24(t,J=8.2Hz,1H),6.05(dd,J=14.6,11.3Hz,1H),5.94(d,J=11.3Hz,1H),5.84 –5.73(m,1H),5.55(dd,J=9.9,2.5Hz,1H),5.42(ddd,J=16.3,11....

Embodiment 3

[0041] Embodiment 3: the preparation of compound 3

[0042] 99mg (0.17mmol) of compound 2 was added to a 10mL single-necked round bottom flask, then 18mL of isopropanol was added for dissolution, then 150mg of 4A molecular sieves were added, and the flask was then placed on an ice bath. Dissolve 244mg (20eq) of hydroxylamine hydrochloride in a small amount of methanol, slowly drop it into a round bottom flask, and react with magnetic stirring for 24h. The progress of the reaction was monitored by TLC. After the reaction was complete, it was extracted three times with anhydrous ether / water (1 / 1, v / v), and the combined organic phase was washed with water until the pH was close to neutral, dried, filtered and spin-dried, and passed through a silica gel column separation column The target compound 3 was obtained, which was the mirbe oxime compound, and the yield was 65%.

[0043] The structure determination data of compound 3 are as follows:

[0044] HRMS(m / z):calc.611.3332,foun...

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Abstract

The invention discloses a milbemycin oxime compound and a preparation method thereof. The compound as shown in a general formula (I) in the specification is prepared by the steps of carrying out hydrolysis reaction on avermectin B1a to remove C13-position glycosyl, oxidizing both C5-position hydroxyl and C13-position hydroxyl into keto through oxidation reaction, and finally converting the two kinds of keto into oximido, wherein the structure of the compound is confirmed by virtue of the mass spectrum and nuclear magnetic resonance analysis testing technology. According to the milbemycin oxime compound and the preparation method, the milbemycin oxime compound is prepared by starting materials which are cheap and easily obtained; the preparation method has the characteristics of mild reaction condition, simpleness in operation process, low cost and higher yield.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and relates to a mirbe oxime compound and a preparation method thereof. Background technique [0002] Abamectin (avermectins) is a 16-membered ring macrolide compound obtained from the fermentation product of Streptomyces (Streptomyces avermitilis MA-4680) by Japanese scientist Omura Satoshi and American Merck Company in 1976. It is an effective Insecticides for insects, mites and parasites are more and more widely used in the world because of their broad spectrum, high efficiency, low toxicity and no environmental pollution. Abamectin components are more, because Abamectin B1a and B1b are difficult to separate in industrial production, so the main component of commercialized Abamectin is the mixture of B1a and B1b, wherein the content of B1a component is about Accounting for 3 / 4, the content of B1b component accounts for about 1 / 4, it is a broad-spectrum, high-efficiency, low-toxic agricultural...

Claims

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Application Information

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IPC IPC(8): C07D493/22
CPCC07D493/22
Inventor 曾小东田孝东洪学传虞沂邓子新赵昌明
Owner WUHAN UNIV
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