Effective synthesis of C-nucleosides with 2′,4′-BNA modification

Effective synthesis of C-nucleosides with 2′,4′-BNA modification
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DOI:
10.1016/s0040-4020(02)00226-0
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发表时间:
2002-04-08
期刊:
影响因子:
2.1
通讯作者:
Imanishia, T
Imanishia, T
中科院分区:
化学3区
文献类型:
--
作者:
Hari, Y;Obika, S;Imanishia, T

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利用四氢呋喃甲醛1与芳香杂环的镁或锂衍生物的偶联反应,再经Mitsunobu环化反应,有效地合成了一些2 ′-O,4 ′-C-亚甲基桥核酸(2 ′,4 ′-BNA)修饰的C-核苷。此外,它是由H-1 NMR谱和X-射线晶体学清楚地表明,在合成的C-核苷糖构象,独立于核碱基,固定在N-型。(C)2002爱思唯尔科技有限公司版权所有。
The effective synthesis of some C-nucleosides with 2'-O,4'-C-methylene bridged nucleic acid (2',4'-BNA) modification was accomplished by using the coupling reaction of a tetrahydrofurancarbaldehyde 1 with the magnesium or lithium derivatives of aromatic heterocycles followed by the Mitsunobu cyclization. Moreover, it was clearly shown by H-1 NMR spectra and X-ray crystallography that the sugar conformation in the synthesized C-nucleosides, independent of the nucleobases, was fixed in N-form. (C) 2002 Elsevier Science Ltd. All rights reserved.