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.

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页码：3051 / 3063

页数：13

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