- Synthetic method of antiviral drug (R,S)-goitrine
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The invention discloses a synthetic method of an antiviral drug (R,S)-goitrine. The synthesis method comprise the following steps: dissolving nitromethane in a proper solvent, adding acrolein, carrying out stirring at a set temperature for a period of time to obtain a solution A, dissolving triethylamine into residual nitromethane to obtain a solution B, dropwise adding the solution B into the solution A for a reaction, carrying out rotary evaporation to remove the solvent and unreacted nitromethane after the reaction is completed, and carrying out column chromatography separation on the obtained mixture to obtain 1-nitro-3-butenyl-2-ol; reducing nitro of the 1-nitro-3-butenyl-2-ol by an iron powder reduction method to obtain 1-amino-3-butenyl-2-ol; and further carrying out a cyclization reaction on the 1-amino-3-butenyl-2-ol with carbon disulfide to generate the (R,S)-goitrine. The synthetic method disclosed by the invention had the advantages of low cost, simple operation, safety andenvironmentally friendliness.
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Paragraph 0016; 0030; 0034; 0039; 0044; 0049
(2019/04/26)
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- Preparation method of 5-vinyl-2-sulfo-oxazolidine
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The invention discloses a preparation method of 5-vinyl-2-sulfo-oxazolidine. The preparation method comprises the following steps: (1) using acrolein and trimethylsilyl cyanide as raw materials for reaction under the catalysis of zinc iodide to obtain 2-[(trimethyorganosilyl)oxy]-3-butenenitrile; (2) in a toluene solution, using a red aluminum solution as a reducing agent and potassium carbonate and methanol as a desiliconizing agent, performing reduction and desiliconization on the 2-[(trimethyorganosilyl)oxy]-3-butenenitrile to obtain 1-amino-3-butene-2-alcohol; (3) enabling the 1-amino-3-butene-2-alcohol to react with carbon disulfide, and using hydrogen peroxide as a desulfurizing agent to obtain the 5-vinyl-2-sulfo-oxazolidine. The fatty chain cyanogroup used in the preparation methodis the red aluminum solution; compared with conventional lithium aluminum hydride, the red aluminum solution has simple operation conditions and is low in cost. In the reduction, methylbenzene, instead of traditional combustible liquid such as diethyl ether and the like, is used as a solvent, so that the reaction conditions are safer. In the annulations in the step (3), the hydrogen peroxide replaces original lead nitrate and serves as the desulfurizing agent, so that the pollution to the environment can be reduced, and the method is safe and environmentally-friendly.
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Paragraph 0023; 0026; 0027; 0030; 0031; 0034
(2019/05/08)
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- A high-purity 5 - vinyl oxazolidine -2 - thione preparation method
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The invention discloses a preparation method of high-purity 5-vinyl oxazolidine-2-thioketone. The preparation method comprises the following steps: carrying out coordination on 1-amino-3-butene-2-alcohol taken as a starting material by using lead nitrate water solution, carrying out annulation on the raw material and CS2 in alkaline environment of potassium hydroxide solution, filtering the reaction liquid, extracting the reaction liquid by using ethyl acetate, carrying out liquid separation, drying and rotary evaporation to obtain a crude product, purifying the water solution containing the crude product through a preparative liquid chromatograph, receiving a mobile phase in the retention time period of a target product, and carrying out rotary evaporation and drying to obtain the product. According to the method, the steps are simple, the operation is convenient, the cost is low and the output is relatively high; and according to the method, the single-pass preparation amount can be up to 0.2-0.3g and the purity is 99.0-99.5%.
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Paragraph 0033-0048
(2017/08/24)
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- The formation of 2-hydroxybut-3-enyl cyanide from (2s)-2-hydroxybut-3-enyl glucosinolate using immobilized myrosinase
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Starting from (2S)-2-hydroxybut-3-enylglucosinolate (epiprogoitrin) isolated from Crambe abyssinica seeds the chiralic 2-hydroxy-3-butenyl cyanide was produced in pure form and acceptable yield, using immobilized myrosinase purified from Sinapis alba on a Nylon 6.6 membrane.
- Leoni,Felluga,Palmieri
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p. 7967 - 7970
(2007/10/02)
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- BIOSYNTHESIS OF 2-HYDROXY-3-BUTENYLGLUCOSINOLATE AND 3-BUTENYLGLUCOSINOLATE IN BRASSICA NAPUS
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Desulpho-3-butenylglucosinolate is considered to be a potential late stage precursor in the biosynthesis of (R)-2-hydroxy-3-butenylglucosinolate (progoitrin) and 3-butenylglucosinolate (gluconapin) in Brassica.Chemically synthesized (β-D-glucopyranosyl)-4-pentenethiohydroxamic acid when administered to developing seedlings of Brassica napus cv Bienvenu was found to be well incorporated into both 2-hydroxy-3-butenylglucosinolate and 3-butenylglucosinolate, while feeding experiments with methionine have shown that de novo biosynthesis is slow.Analysis of seeds and developing seedlings has shown that levels of 2-hydroxy-3-butenylglucosinolate are maintained while 3-butenylglucosinolate levels are considerably reduced.
- Rossiter, J. T.,James, D. C.,Atkins, N.
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p. 2509 - 2512
(2007/10/02)
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- Degradation of 2-Hydroxybut-3-enylglucosinolate (Progoitrin)
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Using a model system consisting of synthesized 2-hydroxybut-3-enylglucosinolate and a purified thioglucoside glucohydrolase preparation from Brassica napus, the effects of ascorbate, of Fe2+ and of Cu2+ were examined on the extent and course of glucosinolate degradation.Ascorbate was found to promote thioglucosidase activity to a considerable extent over the whole of the wide range of concentrations studied (0.024-400 mM), with a maximum (activation factor ca 110) at 1.57 mM ascorbate.Fe2+ slightly suppressed reaction, but caused a significant effect by directing degradation to 1-cyano-2-hydroxybut-3-ene rather than to 5-vinyloxazolidine-2-thione, and at low, catalytic, concentrations.Cu2+ had similar effect, but was a strong inhibitor of the reaction.Key Word Index - Glucosinolates; 2-hydroxybut-3-enylglucosinolate; progoitrin; thioglucoside glucohydrolase.
- MacLeod, Alexander J.,Rossiter, John T.
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p. 669 - 674
(2007/10/02)
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