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5-formacylpyrimidine carbocyclic nucleoside and preparation method thereof

A technology for formylpyrimidine carbocyclic nucleoside and formylpyrimidine carbocyclic nucleoside compound is applied in the field of 5-formylpyrimidine carbocyclic nucleoside and preparation, and achieves the effects of mild reaction conditions, simple operation process and rich reaction performance

Inactive Publication Date: 2012-07-25
HENAN NORMAL UNIV
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At present, there is no report about this type of compound and its preparation method

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  • 5-formacylpyrimidine carbocyclic nucleoside and preparation method thereof
  • 5-formacylpyrimidine carbocyclic nucleoside and preparation method thereof
  • 5-formacylpyrimidine carbocyclic nucleoside and preparation method thereof

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[0036] Example. Synthesis of 5-formyl-2'-deoxyuridine carbocyclic nucleoside (target product a)

[0037] (1) Add 5-methyl-2'-deoxyuridine carbocyclic nucleoside (2.40 g, 10 mmol) and DMAP (0.05 g) into a reaction flask filled with acetic anhydride (15 mL), and stir at room temperature for reaction. After the reaction is complete (monitored by TLC), add absolute ethanol, concentrate, then add a small amount of water, filter with suction, and wash with water to obtain a solid product (3.10 g), namely acetyl-protected 5-methyl-2'-deoxyuria Pyrimidine carbocyclic nucleosides. The yield was 95%.

[0038] (2) Add acetyl-protected 5-methyl-2'-deoxyuridine carbocyclic nucleoside (3.10g, 9.5mmol), potassium persulfate (5.10g) and copper sulfate (0.60g) into acetonitrile (30mL ) and water (30mL), 2,6-lutidine (3.4mL) was added, and the reaction was stirred at 65°C. After the reaction was complete (TLC monitoring), separation by column chromatography gave a white solid product (1.40 g...

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Abstract

The invention discloses a 5-formacylpyrimidine carbocyclic nucleoside and a preparation method thereof. The compound disclosed by the invention is an important intermediate for synthesizing a novel 5-substituted pyrimidine carbocyclic nucleoside medicine in a more complex structure. A 5-methylpyrimidine carbocyclic nucleoside compound, which is used as a raw material, is subjected to hydroxy protection, methyl oxidation, hydroxy protecting group removal and the like to obtain the 5-formacylpyrimidine carbocyclic nucleoside derivative. The invention has the advantages of simple and safe operational process and mild reaction conditions, and is convenient for industrial production.

Description

technical field [0001] The invention relates to a novel non-natural pyrimidine carbocyclic nucleoside derivative, mainly 5-formyl pyrimidine carbocyclic nucleoside and its preparation method. Background technique [0002] Nucleoside compounds play an important role in the research of antiviral drugs, and the structural modification of natural nucleosides is an important means to find new and more effective antiviral drugs. Most of the antiviral drugs currently on the market and in the clinical trial stage are nucleoside derivatives, and nucleoside derivatives have therefore become recognized as compounds with the most antiviral potential. [0003] Carbocyclic nucleosides have attracted a great deal of interest over the past few decades. From a structural point of view, carbocyclic nucleosides replace the D-ribose part of the natural nucleoside with a five-membered carbon ring, which makes the nucleoside structurally changed from the original unstable hemiaminal glycoside li...

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/54
CPCY02P20/55
Inventor 范学森张新迎冯东王国利曲莹莹王洋洋郭胜海何艳贾雪菲
Owner HENAN NORMAL UNIV
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