Synthesis of 4'-substituted cordycepins via benzenesulfenylation at the 4'-position as a key step.

Nucleic acids symposium series (2004) Pub Date : 2009-01-01 DOI:10.1093/nass/nrp050

Yutaka Kubota, Mariko Ehara, Hiroki Kumamoto, Hisashi Shimada, Kazuhiro Haraguchi, Hiromichi Tanaka

引用次数: 1

Abstract

With an aim to synthesize 4'-substituted cordycepins, the 4'-phenylthio precursor 4 was prepared from adenosine through an electrophilic addition to the 3',4'-unsaturated derivative 2 by using NIS/PhSH system. Nucleophilic substitution of 4 with a series of alcohols in the presence of NBS gave the respective 4'-alpha-alkoxy cordycepins 6 as the major stereoisomer. Use of DAST, in stead of alcohol in this reaction, gave the 4'-fluoro analogue 7. The 4'-sulfone derivative 8 obtained by m-CPBA oxidation of 4 was employed for the reaction with organoaluminum reagents. These reactions furnished various types of the 4'-carbon-substituted cordycepins 9.

查看原文

微信好友朋友圈 QQ好友复制链接

本刊更多论文

以4′位苯磺酰化为关键步骤合成4′取代虫草素。

为了合成4′-取代虫草素，采用NIS/PhSH体系，以腺苷为原料，在3′，4′-不饱和衍生物2上进行亲电加成，制备了4′-苯硫代前体4。在NBS存在下，用一系列醇对4进行亲核取代，得到4′-烷氧基虫草素6为主要立体异构体。在这个反应中使用DAST代替醇，得到了4'-氟类似物7。利用m-CPBA氧化4得到的4′-砜衍生物8与有机铝试剂反应。这些反应产生了不同类型的4′碳取代虫草素9。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文去求助

来源期刊

Nucleic acids symposium series (2004)

自引率

0.00%

发文量

期刊最新文献

Chemical methods to study protein-nucleic acid interactions. Development of novel chemical probes to detect abasic sites in DNA. Assessment of the DNA damage using the fluorescence microscope. Exciton-controlled fluorescence: application to hybridization-sensitive fluorescent DNA probe. Multiple activities of c-di-GMP in Pseudomonas aeruginosa.