改进的双光子笼 3-硝基-2-乙基二苯并呋喃的合成及其在一种笼状胸腺嘧啶磷酰胺中的应用。
Improved synthesis of the two-photon caging group 3-nitro-2-ethyldibenzofuran and its application to a caged thymidine phosphoramidite.
机构信息
Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695, USA.
出版信息
Org Lett. 2010 Mar 5;12(5):916-9. doi: 10.1021/ol902807q.
Abstract
A new and efficient route to the recently reported 3-nitro-2-ethyldibenzofuran caging group was developed. Furthermore, its installation on a thymidine phosphoramidite is described. This caging group is efficiently removed through light-irradiation at 365 nm.
摘要
开发了一种新的、有效的方法来制备最近报道的 3-硝基-2-乙基二苯并呋喃笼状基团。此外，还描述了它在胸腺嘧啶核苷亚磷酰胺上的安装。通过在 365nm 光照射可以有效地去除这个笼状基团。
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2
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Mol Biosyst. 2008 Jun;4(6):508-11. doi: 10.1039/b800166a. Epub 2008 Apr 8.
3
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Org Lett. 2007 May 10;9(10):1903-6. doi: 10.1021/ol070455u. Epub 2007 Apr 21.
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