Method for synthesizing and preparing 5'-S-(4, 4'-dimethoxytriphenylmethyl)-2'-deoxyinosine

Abstract

The invention discloses a method for synthesizing and preparing 5'-S-(4, 4'-dimethoxytriphenylmethyl)-2'-deoxyinosine. The method comprises the following steps of: under inert gas protection, carrying out mitsunobu reaction on 2'-deoxyinosine and 4, 4'-dimethoxytriphenylmethyl mercaptan in an organic solvent at room temperature under effects of an azo reagent, a phosphine coordination compound, organic alkali or protonic acid, i.e. carrying out intermolecular dehydration reaction on 5'-hydroxyl of the 2'-deoxyinosine and the 4, 4'-dimethoxytriphenylmethyl mercaptan to obtain a C-S bond, and obtaining the 5'-S-(4, 4'-dimethoxytriphenylmethyl)-2'-deoxyinosine. The method for synthesizing and preparing the 5'-S-(4, 4'-dimethoxytriphenylmethyl)-2'-deoxyinosine has the beneficial effects of being wide in raw material sources, low in price, high in yield, mild in reaction condition, good in selectivity, simple in operation process, convenient in post-treatment, and suitable for large-scale industrial production.

Description

technical field The invention relates to a synthesis and preparation method of 5'-S-(4,4'-dimethoxytrityl)-2'-deoxyinosine in the field of chemical synthesis. Background technique With the development of molecular biology and pharmaceutical industry, the research and development of nucleoside compounds and their derivatives has become a hot spot. With the deepening of research, the new nucleoside compounds obtained after functional group transformation and modification of nucleoside compounds and their derivatives are useful in the treatment of cardiovascular diseases, central nervous system diseases, circulatory and urinary system diseases, as well as antiviral and antitumor. It has a special curative effect and is widely used in molecular biology, medicine and other fields. Structural modification of nucleoside compounds and the introduction of heteroatom sulfur can sometimes greatly improve the antiviral activity of drugs, and at the same time reduce the toxic and side e...

AI Technical Summary

Problems solved by technology

By activating the 5'-hydroxyl of 2'-deoxythymidine with methanesulfonyl chloride, after esterification with potassium thioacetate, 4,4'-dimethoxytriphenylmethylthiol ((MeO) 2 TrSH) (Efficient Solid Synthesis of Cleavable Oligodeoxynucleotides Based on a Novel Strategy for the Syhthesis of 5'-S-(4,4'-Dimethoxytrityl)-2'-deoxy-5'-thionucleoside Phosphramidites, Kerstin Jahn-Hofmann and Ioachin W.Engels, Helvetica Chimica Acta-Vol.87(2004), 2812-2828)), yet this method produces multiple intermediate products through multi-step reactions, and finally obtains 5'-S-(4,4'- The yield of dimethoxytrityl)-2'-deoxythymidine is on the low side, can only reach 38.3%, and wherein the third step has used 1,1,3,3-tetramethylguanidine as catalyst, Expensive, high production cost, not suitable for industrial production

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