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A kind of synthetic method of 2'-deoxyadenosine

A technology of deoxyadenosine and its synthetic method, which is applied in the fields of drug synthesis and intermediate preparation, can solve problems such as inability to apply industrial production, unavoidable column chromatography, difficult industrial production, etc., and achieve simplified operation, low cost and stable product quality Effect

Inactive Publication Date: 2018-08-28
CENT SOUTH UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] The shortcoming of this method is that raw material is rare, operation is difficult, used sodium hydride in the reaction process, causes reaction to be difficult to control, and yield is low (the first step reaction only has 32%, reaction total yield 27.2%), is difficult for industrialized production
[0016] To sum up, there are many existing methods for synthesizing 2'-deoxyadenosine, but most of them cost too much, some raw materials are rare and toxic, some have low yields, some are difficult to operate, and column chromatography is unavoidable. and other shortcomings, so they cannot be applied to large-scale industrial production

Method used

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  • A kind of synthetic method of 2'-deoxyadenosine
  • A kind of synthetic method of 2'-deoxyadenosine
  • A kind of synthetic method of 2'-deoxyadenosine

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Effect test

Embodiment 1

[0073] (1) Synthesis of 2'-O-tosyladenosine (III) from adenosine (I)

[0074] Weigh 1.34g of adenosine, 1.37g of di-n-butyltin oxide, and 35ml of methanol, put the above-mentioned raw materials in a 100ml round bottom flask, heat to reflux for 2h, and the resulting 2',3'-di-n-butylstannylidene Glycoside (II) is directly subjected to the next step reaction, adding 3.10 g of p-toluenesulfonyl chloride and 2 ml of triethylamine to the reaction mixture, stirring and reacting at room temperature for 3-5 h, standing at room temperature for 1 h after the reaction, suction filtering, and washing the filter residue with methanol, and then The filter residue was dried in a vacuum drying oven to finally obtain 1.71 g of white powdery solid 2'-O-p-toluenesulfonyladenosine with a yield of 81.2%. HPLC purity 98.1%.

[0075] (2) Synthesis of 2'-deoxyadenosine (IV) from 2'-O-tosyladenosine (III)

[0076] Weigh 1.69g of 2'-O-p-toluenesulfonyladenosine, 10ml of anhydrous dimethyl sulfoxide, p...

Embodiment 2

[0078] (1) Synthesis of 2'-O-tosyladenosine (III) from adenosine (I)

[0079] Weigh 2.67g of adenosine, 2.99g of di-n-butyltin oxide, and 50ml of methanol, put the above-mentioned raw materials in a 100ml round bottom flask, heat to reflux for 3h, remove the methanol by rotary evaporation after reaction, and generate 2',3'-di n-Butylstannylidene adenosine (II) directly proceeds to the next step reaction, add 3.10g of p-toluenesulfonyl chloride, 2ml of triethylamine, and 50ml of dichloromethane to the reaction mixture, stir and react at room temperature for 5-7h, and rotate to evaporate after reaction Concentrate, add 15ml of methanol, stand at room temperature for 1h, filter with suction, wash the filter residue with methanol, and then dry the filter residue in a vacuum drying oven to finally obtain 3.76g of white powdery solid 2'-O-p-toluenesulfonyladenosine. The rate is 89.2%. HPLC purity 98.6%.

[0080] (2) Synthesis of 2'-deoxyadenosine (IV) from 2'-O-tosyladenosine (III...

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Abstract

The invention discloses a synthesis method for 2'-deoxyadenosine monohydrate. Adenosine is esterified and acylated by an acylating agent and an acid-binding agent so that acylate can be obtained, the acylate is subjected to reduction and purification, and then 2'-deoxyadenosine monohydrate is obtained, wherein in the esterifying process, dialkyl group stannic oxide is adopted as an esterifying agent. According to the method, reaction selectivity is high, chromatographic separation is not needed, cost is low, and the yield is high; the synthesis method is applicable to industrial production.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis and intermediate preparation, and in particular relates to a synthesis method of 2'-deoxyadenosine. Background technique [0002] 2'-deoxyadenosine, also known as 2'-deoxyadenosine (2'-deoxyadenosine, also known as β-D-2'-deoxyadenosine), is a natural deoxyribonucleoside, which is deoxyribose The structural fragments of nucleic acid DNA, like other natural nucleosides, participate in the transmission of genetic information in almost all biological cells, affect the synthesis of proteins and the metabolism of polysaccharides, and have great effects on the growth, proliferation, differentiation and inhibition of cells in organisms. important regulatory role. It is not only an important raw material for gene medicine and genetic engineering research, but also has good physiological activity itself. 2'-Deoxyadenosine can inhibit the release of insulin induced by sugar, and can reduce the speci...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H19/173C07H1/00
CPCC07H1/00C07H19/173
Inventor 钟世安黄燊邓志伟陈建孙燕华胡雨薇李雨晴许江峰刘慧
Owner CENT SOUTH UNIV
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