Synthesis of 4′-Selenoribonucleosides, the Building Blocks of 4′-SelenoRNA, Using a Hypervalent Iodine

Q4 Chemistry
Noriko Saito-Tarashima, Masashi Ota, Noriaki Minakawa
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引用次数: 4

Abstract

Herein is described a detailed protocol for the synthesis of 4′-selenoribonucleoside derivatives that involves the use of a hypervalent iodine species. These derivatives are versatile units for the preparation of 4′-selenoRNA. Large-scale synthesis of a 4-selenosugar starting from D-ribose is achieved in eight steps, including a final chromatographic purification. The resulting 4-selenosugar is then subjected to the one-pot Pummerer-like reaction using hypervalent iodine in the presence of silylated nucleobases. The reaction with silylated uracil affords the desired 4′-selenouridine derivatives with excellent β-selectivity and in good yield. Conversely, when purine nucleobases are used in the Pummerer-like reaction, N7 4′-selenoribonucleoside isomers are obtained alongside the desired N9 isomers. However, the undesired N7 isomers can be converted to the desired N9 ones under acidic conditions. © 2017 by John Wiley & Sons, Inc.

利用高价碘合成4′-硒核苷,作为4′-硒核苷的组成部分
本文描述了合成4 ' -硒核糖核苷衍生物的详细方案,其中涉及使用高价碘种。这些衍生物是制备4′-selenoRNA的通用单元。从d -核糖开始大规模合成4-硒糖需要八个步骤,包括最后的色谱纯化。得到的4-硒糖然后在硅基化核碱基存在的情况下,使用高价碘进行一锅类似于彭默尔的反应。与硅基化尿嘧啶反应得到β选择性好、产率高的4′-硒尿嘧啶衍生物。相反,当嘌呤核碱基用于类pummer反应时,n74 ' -硒核糖核苷异构体与所需的N9异构体一起得到。然而,不需要的N7异构体可以在酸性条件下转化为所需的N9异构体。©2017 by John Wiley &儿子,Inc。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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来源期刊
Current Protocols in Nucleic Acid Chemistry
Current Protocols in Nucleic Acid Chemistry Chemistry-Organic Chemistry
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期刊介绍: Published in association with International Society for Nucleosides, Nucleotides & Nucleic Acids (IS3NA) , Current Protocols in Nucleic Acid Chemistry is equally valuable for biotech, pharmaceutical, and academic labs. It is the resource for designing and running successful research projects in the rapidly growing and changing field of nucleic acid, nucleotide, and nucleoside research.
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