Preparation method of beta-configuration decitabine precursor
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A decitabine and configuration technology, applied in the field of preparation of decitabine precursor, can solve the problem of unfavorable enrichment of β-type products, and achieve the effect of simple post-processing, good repeatability and stable purity
Inactive Publication Date: 2017-08-04
ZHENGZHOU TECHN COLLEGE +1
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[0006] In short, the prior art of directly using methoxy for direct coupling all teaches that it is not conducive to the enrichment o...
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Embodiment 1
[0018] 60mmol of 2,4-bis-(trimethylsilyl)-5-azacytosine and 50mmol of 1-(2-butenyl)oxy-2-deoxy-3,5-di-O-acetyl -D-Ribofuranose was dissolved in 500 mL of acetonitrile, the temperature was controlled to 0°C, 10 mmol of trifluoromethanesulfonic acid was added, and kept at 0°C, the reaction was stirred for 2 hours, and the reaction was completed by HPLC monitoring. Quickly quench the reaction and wash the reaction mixture with 500 mL saturated aqueous sodium bicarbonate solution, separate the organic layer, evaporate it to dryness under vacuum, and then recrystallize with toluene to obtain 14.75 g of solid, which is identified as 1-(2- Deoxy-3,5-di-O-acetyl-D-ribose)-4-amino-1,3,5-s-triazin-2-one, its purity is 90% by HPLC, wherein the β configuration and α The content ratio of the configuration is 2.5.
[0021] Use 1-allyloxy-2-deoxy-3,5-di-O-acetyl-D-ribofuranose to directly carry out the coupling reaction, and each condition refers to the example cytosine raw material 1,2,4-di-( The amount of trimethylsilyl)-5-azacytosine is different, and the results are summarized as follows:
[0022]
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Abstract
The invention provides a preparation method of a beta-configuration decitabine precursor. The preparation method comprises the following step: under the action of a Lewis acid catalyst, directly performing a coupling reaction on acylated sugar adopting the structure of 1-alkenylmethoxy-2-deoxy-3, 5-di-O-acetyl-D-ribofuranose and a silicon ether compound of 5-azacytosine to obtain beta-configuration 1-(2-deoxy-3,5-di-O-acetyl-D-ribose)-4-amino-1,3,5-s-triazine-2-one. The beta-configuration decitabine precursor is high in selectivity, good in repeatability and very high in molar yield and purity.
Description
technical field [0001] The invention relates to a preparation method of decitabine precursor. Background technique [0002] The preparation process of decitabine is disclosed in many documents, and it is roughly divided into three categories: isocyanate method, azacitidine deoxygenation method, and glycosidation method. The characteristic of glycosidation method is to couple the pyrimidine part with the ribose part. The coupling reaction is The product of the decitabine is hydroxyl-protected decitabine (this application is called decitabine precursor), and finally decitabine is obtained through deprotection (usually hydrolysis). As we all know, decitabine is a β-type isomer, but the mixture of α and β is usually obtained during preparation. Obviously, the content ratio of β-type decitabine in the product and the complexity of purification Both are directly affected by the proportion of the β-form in the decitabine precursor before hydrolysis. [0003] Before coupling, ribo...
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