Novel method for synthesizing 5-carboxyl-2'-deoxycytidine

A deoxycytidine and carboxyl technology, applied in chemical instruments and methods, preparation of sugar derivatives, sugar derivatives, etc., can solve the problems of expensive raw materials, etc., and achieve simple synthesis methods, high product yields, and cheap and easy-to-obtain raw materials Effect
CN104592333AInactive Publication Date: 2015-05-06JIANGXI SCI & TECH NORMAL UNIV
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
JIANGXI SCI & TECH NORMAL UNIV
Publication Date
2015-05-06
Estimated Expiration
Not applicable · inactive patent

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Abstract

The invention relates to a method for synthesizing 5-carboxyl-2'-deoxycytidine. The method comprises the following steps: 1) brominating 3', 5'-biTBS deoxythymidine by using an N-bromo-succinimide NBS/azodiisobutyronitrile (AIBN) system to obtain a bromo intermediate and carrying out in-situ acetate substitution to obtain an acetyl protective intermediate (3); 2) aminating a nucleoside base by using a paratoluensulfonyl chloride/N-methylpiperidine/triethylamine and ammonia water system to obtain an acetyl protected hydroxymethyl deoxycytidine precursor (4); 3) removing acetyl under an alkaline condition by using potassium carbonate to obtain a hydroxymethyl precursor (5); and 4) oxidizing the hydroxymethyl precursor (5) by using a 2, 2, 6, 6-tetramethyl piperidine-nitro-oxide (TEMPO)/iodobenzene diacetate (BAIB) oxidizing system and removing the TBS protective group under the TFA condition to obtain a target object. The method provided by the invention has the advantages of simple method and high yield.
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Description

technical field

[0001] The invention belongs to the field of chemical synthesis and relates to a novel synthesis method for synthesizing 5-carboxy-2'-deoxycytidine by protecting deoxythymidine raw materials with double TBS. technical background

[0002] In mammalian genes, 5-methyl-2'-deoxycytidine is a low-content nucleoside, accounting for only about 1% of the total DNA nucleosides. The latest research shows that 5-methyl-2'-deoxycytidine can be oxidized to 5-hydroxymethyl-2'-deoxycytidine, 5-formyl-2'-deoxycytidine and 5-formyl-2'-deoxycytidine under the action of special oxidase -Carboxy-2'-deoxycytidine. These three nucleoside oxides are thought to be involved in the regulation of cellular epigenetic programs. Therefore, the synthesis of oligonucleotides and triphosphates from 5-carboxy-2'-deoxycytidine and other 5-methyl-2'-deoxycytidine oxides as raw materials and molecular biological research on the regulation of epigenetic programs has important meaning. However...

Claims

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