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Synthesis method of nucleoside compound and intermediate of nucleoside compound

A nucleoside and ribose technology, applied in the field of chemistry, can solve the problems of unfavorable large-scale synthesis, low X1 yield and high synthesis cost, and achieve the effects of improving reaction yield, easy solubility and good solubility

Pending Publication Date: 2020-02-21
GUANGZHOU RIBOBIO
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  • Application Information

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Problems solved by technology

This method still contains about 10% of X2 impurities, and the yield of X1 is also low, and the synthesis cost is high, which is not conducive to large-scale synthesis

Method used

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  • Synthesis method of nucleoside compound and intermediate of nucleoside compound
  • Synthesis method of nucleoside compound and intermediate of nucleoside compound
  • Synthesis method of nucleoside compound and intermediate of nucleoside compound

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Embodiment 1

[0072] Step 1, the synthesis of X6 (2,9-diacetylguanine)

[0073] Dissolve 10gX5 (guanine) in 85mL N,N-dimethylacetamide, then add 20mL acetic anhydride Ac 2 O, under the protection of nitrogen, the temperature was raised to 165°C for 17h. After the reaction of the raw materials was complete, the reaction solution was cooled to room temperature and allowed to stand for 12 hours to crystallize, and a large amount of solids precipitated out. The product X6 (2,9-diacetylguanine) was filtered and dried to obtain 14.3 g, with a yield of 92.1%.

[0074] 1 HNMR (500MHz, DMSO-d6) δ: 2.19 (s, 3H), 2.80 (s, 3H), 8.30 (s, 1H), 11.68 (br s, 2H); 13CNMR (DMSO-d6, 75.5MHz) δ: 23.9, 24.7, 121.7, 137.7, 147.3, 154.9, 168.3, 173.6, 174.0; MS (ESI), m / z: 235.20 ([M+H]+).

[0075] Wherein, X5 (guanine) structural formula is:

[0076]

[0077] The structural formula of X6 (2,9-diacetylguanine) is:

[0078]

[0079] Step 2, the synthesis of X7 (2-acetyl-6-oxodibenzamide-guanine)

[008...

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Abstract

The invention provides a synthesis method of a nucleoside compound and an intermediate of the nucleoside compound. According to the method, a protection group is introduced to guanine position-6 ketone carbonyl, then only the position-9 N atom of the prepared guanine derivative attacks annular oxonium ions of ribose, and guanine locked nucleoside is synthesized after reactions such as nucleoside locking and deprotection, so that side reaction products can be reduced, and the yield of a final product can be increased.

Description

technical field [0001] The invention relates to the technical field of chemistry, in particular to a method for synthesizing nucleoside compounds and their intermediates. Background technique [0002] Locked nucleic acid (LNA) is a bicyclic nucleotide derivative, and its ring formation method includes the formation of an oxymethylene bridge ring through the shrinkage of the 2'-O and 4'-C positions of ribose. The double ring structure makes the locked nucleic acid have many superior properties. For example, compared with other oligonucleotide analogs, locked nucleic acid has stronger stability and higher hybridization affinity, and can be used in gene detection, gene therapy, etc. At the same time, partially or fully modified LNA oligonucleotide chains can be synthesized on an automatic DNA synthesizer by the phosphoramidate method. [0003] There are currently several methods for synthesizing guanine-locked nucleic acid (LNA-G-locked nucleic acid). The more classic one is ...

Claims

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Application Information

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IPC IPC(8): C07H1/00C07H19/16
CPCC07H1/00C07H19/16C07H19/00Y02P20/55
Inventor 张必良赵浩廷王玮吴乃幸
Owner GUANGZHOU RIBOBIO
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