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Phosphoramidite nucleoside derivative as well as synthesis method, application and kit thereof

A technology of nucleoside derivatives and synthesis methods, applied in the direction of sugar derivatives, sugar derivatives, sugar derivatives preparation, etc., which can solve the problems of limiting the research and application of oligonucleotide drugs, high preparation costs, and difficulty in purification. Achieve good industrial application value, facilitate mass production, and be easy to purify

Pending Publication Date: 2022-04-12
SHANGHAI ZHAOWEI TECH DEV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The current chemical synthesis process has the low purity of the initial product, it is difficult to purify, and the cost of mass production is very high, which greatly limits the research and application of oligonucleotide drugs

Method used

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  • Phosphoramidite nucleoside derivative as well as synthesis method, application and kit thereof
  • Phosphoramidite nucleoside derivative as well as synthesis method, application and kit thereof
  • Phosphoramidite nucleoside derivative as well as synthesis method, application and kit thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0084] Synthesis of intermediate c:

[0085]

[0086] Steps:

[0087] Dissolve compound b (190g, 0.756mol, 1.0eq.) in pyridine (1.9L), add TMSCl (329g, 3.024mol, 4.00eq.), and react at 25±5°C for 2 hours.

[0088] Then add Bz 2 O (dibenzoyl peroxide, 342g, 1.512mol, 2.0eq.), the reaction solution was heated to 60±5°C and stirred for 8 hours, then added water (400mL) and stirred for 1 hour.

[0089] Subsequently, the reaction solution was directly concentrated to dryness, reconstituted by adding EA (ethyl acetate, 1.9 L), and washed with water (1 L) each time, twice in total. After washing, liquid separation was carried out, and the separated organic phase was dried with anhydrous sodium sulfate and concentrated to dryness at 35±5°C to obtain a crude product. The crude product was suspended and stirred in EtOH / EA (ethanol:ethyl acetate; 1.8L / 0.2L) for 30 minutes, filtered, and dried in vacuo to obtain 200g of compound c, with an HPLC purity of 98.5% and a molar yield of 74%...

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Abstract

The invention discloses a phosphoramidite nucleoside derivative as well as a synthesis method, application and a kit thereof, and belongs to the field of oligonucleotides. The synthesis method comprises the following steps: protecting hydroxyl of an initiator, protecting N6-site amino on a basic group, and then removing protection of 3 'and 5' hydroxyl to obtain a first intermediate; protecting 5'and 3 'hydroxyl groups of the first intermediate to obtain a second intermediate; removing a protecting group of 5'hydroxyl of the second intermediate, and protecting the 5 'hydroxyl through methoxy isopropyl to obtain a third intermediate; sequentially removing protecting groups of 3'hydroxyl and N6 amino on the basic group in the third intermediate to obtain a fourth intermediate; and carrying out imidization protection on an N6-site amino group on a basic group of the fourth intermediate, and carrying out phosphoramidation protection on a 3 '-hydroxyl group. The method has the advantages of being convenient to implement, economical and capable of achieving large-scale production.

Description

technical field [0001] The application relates to the field of oligonucleotides, in particular, to a phosphoramidated nucleoside derivative and its synthesis method, application and kit. Background technique [0002] So far, for diseases such as cancer and viral infection, there is still a lack of ideal specific drugs clinically. Fortunately, with the completion of genome sequencing of humans and important model organisms, as well as the in-depth study of functional genomics and proteomics, molecular targets related to diseases have been continuously discovered and understood, which provides a prerequisite for gene therapy. [0003] In the past few decades, synthetic oligonucleotides have been widely used in the research of targeted gene therapy. Oligonucleotides mainly include antisense oligonucleotides (ASODN), small interfering RNA (Small interference RNA, siRNA), transcription factor decoy (Decoy), ribozyme (Ribozyme), deoxyribozyme (DNAzyme) , Antigene (Antigene), CpG...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/073C07H1/00
Inventor 王晨李文强陈哲贤刘建新黄银军杨阳姚峰
Owner SHANGHAI ZHAOWEI TECH DEV
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