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一种用于乙烯基膦酸酯连接核酸的烯烃交叉复分解方法。

An olefin cross-metathesis approach to vinylphosphonate-linked nucleic acids.

作者信息

Lera M, Hayes C J

机构信息

The School of Chemistry, The University of Nottingham, University Park, Nottingham, NG7 2RD, UK.

出版信息

Org Lett. 2001 Aug 23;3(17):2765-8. doi: 10.1021/ol016366d.

DOI:10.1021/ol016366d
PMID:11506629
Abstract

[reaction: see text]. The synthesis of vinylphosphonate-linked nucleotide dimers has been achieved using an olefin cross-metathesis (CM) reaction as a key step. The 1,3-dimesityl-4,5-dihydroimidazol-2-ylidine-containing catalyst 5 (Grubbs' second-generation catalyst) was found to be the superior catalyst for this transformation. Both metathesis partners were readily available using known methodology, and the vinylphosphonate-linked dimer was produced with high levels of (E)-selectivity (>20:1) in 58% yield (70% based on recovered starting material).

摘要

[反应:见正文]。以烯烃复分解(CM)反应为关键步骤,实现了乙烯基膦酸酯连接的核苷酸二聚体的合成。发现含1,3 - 二甲基苯基 - 4,5 - 二氢咪唑 - 2 - 亚基的催化剂5(格拉布第二代催化剂)是该转化反应的优良催化剂。两种复分解反应物均可通过已知方法轻松获得,并且以58%的产率(基于回收的起始原料为70%)、高(E)-选择性(>20:1)生成了乙烯基膦酸酯连接的二聚体。

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J Org Chem. 2011 Jun 3;76(11):4697-702. doi: 10.1021/jo200360s. Epub 2011 Apr 29.