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Preparation method for cytidine

A technology of cytidine nucleoside and cytosine, which is applied in the field of organic chemical synthesis, can solve the problems of high price and unsuitability for industrial production, and achieve the effect of low price, low cost and simple process steps

Inactive Publication Date: 2012-09-26
SHANGYU HUAKE CHEM +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The starting material of this method is acylcytosine, which is more expensive than cytosine and is not suitable for industrial production

Method used

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  • Preparation method for cytidine
  • Preparation method for cytidine
  • Preparation method for cytidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Add 10g (0.09mol) of cytosine and 150mg of ammonium sulfate into a 250ml three-necked flask, keep it dry, pass nitrogen gas into the three-necked flask, then add 30g (0.20mol) of tert-butyldimethylsilyl chloride, and stir slowly. After the addition was completed, the temperature was raised to 120° C. for 8 hours, and the reaction was completed. The product N-(tert-butyldimethylsilyl)-2-(tert-butyldimethylsilyloxy)-4-pyrimidinamine is obtained. The product was dissolved with 100 ml of chloroform.

[0048] In a 250ml three-necked flask, add 35g (0.11mol) of tetraacetylribose and 10ml of chloroform and stir to dissolve, add dropwise 32g of titanium tetrachloride, and dropwise add N-(tert-butyl dichloride) at an ambient temperature of 20°C Methylsilyl)-2-(tert-butyldimethylsilyloxy)-4-pyrimidinamine in chloroform, dropwise, stirred for 2h. After the reaction is complete, add 15ml of water, stir for 2 hours to quench, filter, and the filtrate is dried with anhydrous sodium...

Embodiment 2

[0053] Add 10g (0.09mol) of cytosine and 200mg of ammonium sulfate to a 250ml three-necked flask, keep it dry, pass helium into the three-necked flask for protection, then add 27g (0.18mol) of tert-butyldimethylsilyl chloride, and stir slowly . After the addition was completed, the temperature was raised to 110°C and the reaction was kept for 10 hours, and the reaction was completed. The product N-(tert-butyldimethylsilyl)-2-(tert-butyldimethylsilyloxy)-4-pyrimidinamine is obtained. The product was dissolved with 100 ml of chloroform.

[0054] In a 250ml three-necked flask, add 50g (0.135mol) of tetraacetylribose and 20ml of chloroform and stir to dissolve, add dropwise 60g of titanium tetrachloride, and dropwise add N-(tert-butyldi Methylsilyl)-2-(tert-butyldimethylsilyloxy)-4-pyrimidinamine in chloroform, dropwise, stirred for 5h. After the reaction is complete, add 15ml of water, stir for 2 hours to quench, filter, and the filtrate is dried with anhydrous sodium sulfate ...

Embodiment 3

[0059] Add 10g (0.09mol) of cytosine and 100mg of ammonium sulfate to a 250ml three-necked flask, keep it dry, pass nitrogen into the three-necked flask, then add 40.5g (0.27mol) of tert-butyldimethylsilyl chloride, and stir slowly . After the addition was completed, the temperature was raised to 130° C. for 6 hours, and the reaction was completed. The product N-(tert-butyldimethylsilyl)-2-(tert-butyldimethylsilyloxy)-4-pyrimidinamine was obtained. The product was dissolved with 100 ml of chloroform.

[0060] In a 250ml three-necked flask, add 28.6g (0.09mol) of tetraacetylribose and 10ml of chloroform and stir to dissolve, add dropwise 28.6g of titanium tetrachloride, and dropwise add N-(tert-butyl Dimethylsilyl)-2-(tert-butyldimethylsilyloxy)-4-pyrimidinamine in chloroform, after dropping, stir for 3.5h. After the reaction is complete, add 15ml of water, stir for 2 hours to quench, filter, and the filtrate is dried with anhydrous sodium sulfate and then spin-dried to obta...

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Abstract

The invention discloses a preparation method for cytidine. The method includes following steps: firstly, subjecting cytosine to silanization protection by tert-butyl dimethyl chloro silane; secondly, reacting with tetra-o-acetyl-d-ribose; thirdly, obtaining crude cytidine by ammonolysis of the reactant; and fourthly, adding the crude cytidine to ethanol for refinement, heating, refluxing and dissolving while stirring and adding water, devitrifying after cooling, separating to obtain solid, and drying to obtain the cytidine. The preparation method for the cytidine is simple in process route, low in cost, low in environmental pollution and safe in production, is a route suitable for industrial production and has wide application prospect.

Description

technical field [0001] The invention relates to the field of organic chemical synthesis, in particular to a preparation method of cytidine nucleoside. Background technique [0002] Cytidine, also known as citicoline, cytosine diphosphate choline, diphosphocholine, nicoline, citicoline, nicoline, nicoline or cytidine. It consists of cytosine (the base part) and ribose (the sugar part). Its structural formula is as follows: [0003] [0004] At present, there are many methods for synthesizing cytidine nucleoside (cytidine), as follows: [0005] (1) The method proposed by Nishimara et al. in 1964, using silicon etherification protected N 4 -Acetylcytosine reacts with 1-chlorotriphenylformyl ribose under heating and reflux conditions to generate mixed configuration cytidine, and then the two isomers are separated by recrystallization and column chromatography. Its synthetic route is as follows figure 1 shown. [0006] Wherein, Bz is phenylformyl; [0007] The disad...

Claims

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Application Information

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IPC IPC(8): C07H19/067C07H1/00
Inventor 张江林张家聪葛永明
Owner SHANGYU HUAKE CHEM
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