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A kind of alpha nucleoside synthesis method

A technology for α-nucleosides and compounds, which is applied in the field of nucleoside compound synthesis, and can solve problems such as poor versatility and inapplicability

Active Publication Date: 2021-04-23
SHANGHAI ZHAOWEI TECH DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method can obtain α-cytidine and α-uridine with very good selectivity, but it is not suitable for the synthesis of adenosine and guanosine in α-configuration, so its versatility is not strong

Method used

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  • A kind of alpha nucleoside synthesis method
  • A kind of alpha nucleoside synthesis method
  • A kind of alpha nucleoside synthesis method

Examples

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Effect test

preparation example Construction

[0034] Specifically, the preparation method of the alpha nucleoside provided by the present invention comprises steps:

[0035] In the first step, the hydroxyl group on the raw material 5-O-tert-butyldimethylsilane-2,3-O-isopropylidene-D-ribofuranose is chlorinated to obtain the compound of formula II, and the reaction solution is directly For the next step reaction;

[0036] In the second step, under the action of an inorganic base, the reaction solution prepared from the compound of formula II is coupled with the base to obtain the compound of formula III;

[0037] The third step is to deprotect the compound of formula III under the action of a catalyst to obtain the alpha nucleoside with the structure shown in formula I.

[0038] The synthetic route is:

[0039]

[0040] The reaction in the above-mentioned first step is a solvent with tetrahydrofuran, carbon tetrachloride is a chlorination reagent, and three (dimethylamino) phosphine is a promotor; Carbon tetrachloride...

Embodiment 1

[0080] Synthesis of α-adenosine

[0081] (1) Synthetic compound A crude product

[0082] Concentrate 100g of 5-O-tert-butyldimethylsilane-2,3-O-isopropylidene-D-ribofuranose with acetonitrile to remove water several times, and control the moisture to be less than or equal to 300ppm; under the protection of argon, the 5 -O-tert-butyldimethylsilane-2,3-O-isopropylidene-D-ribofuranose was dissolved in 1000mL THF, the air was replaced 3 times, the temperature of the system was lowered to -70±5°C, and the 75.8g of carbon tetrachloride; 69.6g of tris(dimethylamino)phosphine was added dropwise to the reaction solution, and the addition temperature was controlled at -70±5°C. The temperature of the reaction solution was controlled at -70±5°C and stirred for 1 hour; after 1 hour, the reaction solution was warmed to -40±3°C and stirred for 2 hours to obtain a reaction solution containing compound II, which was designated as reaction solution 1. Under the protection of argon, suspend 41...

Embodiment 2

[0088] Synthesis of α-guanosine

[0089] (1) Synthetic compound C crude product

[0090] Concentrate 100g of 5-O-tert-butyldimethylsilane-2,3-O-isopropylidene-D-ribofuranose with acetonitrile to remove water several times, and control the moisture to be less than or equal to 300ppm; under the protection of argon, the 5 -O-tert-butyldimethylsilane-2,3-O-isopropylidene-D-ribofuranose was dissolved in 1000mL THF, the air was replaced 3 times, the temperature of the system was lowered to -70±5°C, and the 75.8g of carbon tetrachloride; 69.6g of tris(dimethylamino)phosphine was added dropwise to the reaction solution, and the addition temperature was controlled at -70±5°C. The temperature of the reaction solution was controlled at -70±5°C and stirred for 1 hour; after 1 hour, the reaction solution was warmed to -40±3°C and stirred for 2 hours to obtain a reaction solution containing compound II, which was designated as reaction solution 1. Under the protection of argon, suspend 45...

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Abstract

The invention discloses a method for synthesizing alpha nucleosides. The method comprises the steps of: (1) chlorinating the hydroxyl group on 5-O-tert-butyldimethylsilane-2,3-O-isopropylidene-D-ribofuranose having a structure as shown in formula IV to obtain The reaction solution containing the compound shown in formula II; (2) coupling the reaction solution containing the compound shown in formula II with a base to obtain the compound shown in formula III; and (3) making the compound shown in formula III The deprotection of the compound represented by formula III yields the α-nucleoside with the structure represented by formula I.

Description

technical field [0001] The invention belongs to the technical field of nucleoside compound synthesis, and more specifically, the invention relates to a new method for synthesizing alpha nucleosides. Background technique [0002] Antisense technology (Antisense Technology) is based on the principle of base complementarity, using artificially synthesized or biologically synthesized specific DNA or RNA fragments to inhibit or block gene expression, and is a new drug development method. In 1990, Debart et al first reported the synthesis of oligomeric α-uracil nucleotides and confirmed that it can prevent the non-specific degradation of various proteases (Debart F, Rayner B, Imbach JL. Tetrahedron Lett., 1990, Vol.31, No.25, 3537-3540). The important monomer for constructing α-configuration oligonucleotides is α-nucleoside (Wang Shengqi, Ma Liren. Journal of Academy of Military Medical Sciences, 1991; 15:191). [0003] For the synthesis of alpha nucleosides, two methods are rep...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H19/167C07H1/00C07H19/16C07H23/00
CPCC07H1/00C07H19/16C07H19/167C07H23/00
Inventor 赵谦益
Owner SHANGHAI ZHAOWEI TECH DEV
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