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

被引：34
|
作者：
Hari, Y
Obika, S
Sakaki, M
Morio, KI
Yamagata, Y
Imanishia, T
机构：
[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan
[2] Kumamoto Univ, Grad Sch Pharmaceut Sci, Kumamoto 8620973, Japan
来源：
TETRAHEDRON | 2002年 / 58卷 / 15期
基金：
日本学术振兴会;
关键词：
nucleosides; nitrogen heterocycles; Grignard reaction; Mitsunobu reaction;
D O I：
10.1016/S0040-4020(02)00226-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：3051 / 3063
页数：13
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