• 主题
高级搜索  >
历史搜索 清空历史
首页> 外文期刊>Current Protocols in Nucleic Acid Chemistry >Synthesis of Truncated Carbocyclic Nucleosides Using 5'-Deoxy-5'-Heteroarylsulfonylnucleosides
【24h】

Synthesis of Truncated Carbocyclic Nucleosides Using 5'-Deoxy-5'-Heteroarylsulfonylnucleosides

机译：Synthesis of Truncated Carbocyclic Nucleosides Using 5'-Deoxy-5'-Heteroarylsulfonylnucleosides

获取原文
获取原文并翻译 | 示例
           
页面导航
  • 摘要
  • 著录项
  • 相关主题

摘要

This article describes the detailed protocol for the synthesis of "truncated" carbocyclic nucleosides with a cyclopentene core and without a 4'-hydroxymethyl group. The synthesis was performed using 5'-deoxy-5'-heteroarylsulfonylnucleosides, which were prepared by the 5'-O-mesylation of the appropriately protected nucleosides, followed by a nucleophilic substitution with heteroarylthiols and the oxidation of the resulting 5'-S-heteroaryl-5'-thionucleosides. The treatment of the 5'-deoxy-5'-heteroarylsulfonylnucleosides with 1,8-diazabicyclo[5.4.0]undec-7-ene affords the truncated carbocyclic nucleosides, presumably via a domino reaction involving the α-deprotonation of the heteroarylsulfone, elimination of the nucleobase, formation of an α,β-unsaturated sulfone, Michael addition of the nucleobase to the α,β-unsaturated sulfone, and an intramolecular Julia-Kocienski reaction. This protocol would be useful for the short-step synthesis of biologically active carbocyclic nucleosides.

著录项

获取原文

客服邮箱：kefu@zhangqiaokeyan.com

京公网安备：11010802029741号 ICP备案号：京ICP备15016152号-6 六维联合信息科技 (北京) 有限公司©版权所有

  • 客服微信

  • 服务号