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Preparation method of 23-ketoabamectin B2a/B2b derivative

A technology of ketoabamectin and derivatives, applied in the field of organic synthesis reaction

Pending Publication Date: 2021-12-03
HEBEI VEYONG BIO CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But according to this method to react, can only get very little target product

Method used

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  • Preparation method of 23-ketoabamectin B2a/B2b derivative
  • Preparation method of 23-ketoabamectin B2a/B2b derivative
  • Preparation method of 23-ketoabamectin B2a/B2b derivative

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Experimental program
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Embodiment 123

[0051] The synthesis of embodiment 1 23-ketoabamectin B2a / B2b

[0052] 10g (0.01mol) 95% abamectin B2a / B2b, add in 50g methylene chloride, cool to -20 ℃, add 2.4g (0.022mol) trimethylchlorosilane, slowly drop tetramethyl ethyl 2.6g (0.022mol) of ethylenediamine, after the dropwise addition, keep warm at -10~0℃ for 0.5h, then add 2.4g (0.02mol) of tetramethylethylenediamine, 1.6g (0.02mol) of dimethyl sulfoxide, Add 4.2 g (0.02 mol) of phenyl phosphate dichloride dropwise. After the drop is completed, the temperature rises slowly to 0-10°C and keeps warm for 2 hours. Add 1% aqueous sodium hydroxide solution to adjust the pH value to 7-8, separate layers, and the organic phase Add 1.2g (0.01mol) of trifluoroacetic acid to the mixture, stir at room temperature for 2h, wash with water, separate the water phase, and distill off the organic phase to dichloromethane to obtain 9.0g of an off-white solid with a 23-ketoabamectin B2a / B2b content of 95.6 %, yield 90.7%.

[0053] Proton ...

Embodiment 223

[0057] The synthesis of embodiment 2 23-ketoabamectins B2a / B2b

[0058] Add 10g (0.01mol) 95% abamectin B2a / B2b into 50g dichloromethane, cool to -10°C, add 4.5g (0.03mol) triethylchlorosilane, drop tetramethylethylenediamine 3.5g (0.03mol), after dropwise addition, keep warm at 0~10℃ for 2h, then add 2.4g (0.02mol) of tetramethylethylenediamine, 2.4g (0.03mol) of dimethyl sulfoxide, dropwise add phenyl phosphate Diacyl chloride 4.2g (0.02mol), after dripping, the temperature was slowly raised to 20°C, kept for 1h, added 1% aqueous sodium hydroxide solution to adjust the pH value to 7-8, separated, added 0.6g trifluoroacetic acid to the organic phase (0.005mol), stirred at room temperature for 2h, washed with water, separated the water phase, dichloromethane was evaporated from the organic phase to obtain 8.7g off-white solid, 23-ketoabamectin B2a / B2b content 93.9%, yield 86.2%.

[0059] Proton nuclear magnetic resonance spectrum and mass spectrometry analysis result are the ...

Embodiment 3

[0062] Example 3 The synthesis of 4 "-acetamido-23-ketone abamectin B2a / B2b

[0063] Add 10g (0.01mol) 96.0% 4”-acetamidoabamectin B2a / B2b into 50g dichloroethane, cool to -20°C, add 1.1g (0.01mol) trimethylchlorosilane, slowly Add 1.2g (0.01mol) of tetramethylethylenediamine dropwise, after the dropwise addition, keep warm at -10~0℃ for 2h, then add 2.4g (0.02mol) of tetramethylethylenediamine, 1.6g of dimethyl sulfoxide (0.02mol), dropwise add 3.2g (0.015mol) of phenyl phosphate dichloride, dropwise, the temperature rises slowly to 10°C, keep warm for 2h, add 1% aqueous sodium hydroxide solution to adjust the pH value to 7-8, separate layers , adding 0.6 g (0.005 mol) of trifluoroacetic acid to the organic phase, stirring at room temperature for 2 h, washing with water, separating the water phase, and distilling dichloromethane from the organic phase to obtain 8.5 g of light yellow solid, 4”-acetamido-23- The content of ketoabamectin B2a / B2b is 93%, and the yield is 83.3%. ...

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Abstract

The invention discloses a preparation method of a 23-ketoabamectin B2a / B2b derivative. The preparation method comprises the following steps that an abamectin B2a / B2b derivative with at least one hydroxyl group at the 5'positions and 4'positions reacts with alkylchlorosilane to obtain a protected abamectin B2a / B2b derivative; an oxidizing agent is added to oxidize 23-hydroxyl into carbonyl; and finally a protecting group is removed under an acidic condition to obtain a target product as shown in a formula I. The preparation method is simple and easy to operate, and the condition that 23-carbonyl is reduced into hydroxyl in a traditional deprotection method is avoided.

Description

technical field [0001] The invention relates to a preparation method of 23-ketoabamectin B2a / B2b derivatives, belonging to the field of organic synthesis reactions. Background technique [0002] With the in-depth research on abamectin series compounds, the abamectin B2 series compounds with high content can be isolated at present. The study found that abamectin B2 series compounds and abamectin B1 series compounds have different insecticidal spectrum and insecticidal effect, so it has high research significance. [0003] Such as Abamectin B2a has good insecticidal activity to underground nematodes. After medication, Abamectin B2a is metabolized into 23-ketoabamectin B2a. Further research on 23-ketoabamectin B2a yields 23 -Ketoabamectin B2a / B2b derivatives. It is found that 23-ketoabamectin B2a / B2b derivatives such as compound formula I also have certain insecticidal activity on pests, so they have great research value. [0004] [0005] in: [0006] in: [0007] R 1 ...

Claims

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Application Information

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IPC IPC(8): C07H17/08C07H1/00
CPCC07H17/08C07H1/00Y02P20/55
Inventor 田学芳杨泽宇王博张明珠侯红欣贾成国
Owner HEBEI VEYONG BIO CHEM