2016年10月
Practical synthesis of 4 '-selenopurine nucleosides by combining chlorinated purines and 'armed' 4-selenosugar
TETRAHEDRON
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- 巻
- 72
- 号
- 41
- 開始ページ
- 6589
- 終了ページ
- 6594
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1016/j.tet.2016.08.071
- 出版者・発行元
- PERGAMON-ELSEVIER SCIENCE LTD
The synthesis of a variety of chemically modified oligonucleotides requires the development of a practical synthetic method for its building block, i.e., nucleoside analogs. The one-pot Pummerer-like reaction using hypervalent iodine in combination with 6-chloropurine and an 'armed' 4-selenosugar bearing an electron-donating group at the 2-position gave the desired 4'-seleno-6-chloropurine derivative in higher yield as compared to the previous method using a 'disarmed' 4-selenosugar bearing an electron withdrawing group at the 2-position. In addition, the use of 2,6-dichloropurine as a nucleobase transformable into guanine skeleton enabled an effective Pummerer-like reaction followed by isomerization to the desired N9 isomer under the acidic conditions. This Pummerer-like reaction between chlorinated purine bases and an 'armed' 4-selenosugar is advantageous because it affords 4'-selenopurine nucleosides in one-pot without the need for isolation of the unstable selenoxide derivative. (C) 2016 Elsevier Ltd. All rights reserved.
- リンク情報
- ID情報
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- DOI : 10.1016/j.tet.2016.08.071
- ISSN : 0040-4020
- Web of Science ID : WOS:000384776300039