A novel class of modified nucleosides: Synthesis of alkylidene isoxazolidinyl nucleosides containing thymine

被引：18

作者：

Piperno, Anna

Rescifina, Antonio

Corsaro, Antonino

Chiacchio, Maria A.

Procopio, Antonio

Romeo, Roberto

机构：

[1] Univ Messina, Dipartimento Farmacochim, I-98168 Messina, Italy

[2] Univ Catania, Dipartimento Sci Chim, I-95125 Catania, Italy

[3] Magna Graecia Univ Catanzaro, Dipartimento Sci Farmaco Biol, I-88021 Roccelletta Di Borgia, Cz, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 2007卷 / 09期

关键词：

dipolar cycloaddition; nucleosides; nitrogen heterocycles; oxygen heterocycles;

D O I：

10.1002/ejoc.200600817

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of hitherto unknown 1-[3-(hydroxymethyl)-2-methyl-4-methyleneisoxazolidin-5-yl]thymine (5), 1-{(Z)-[3(hydroxymethyl)-2-methylisoxazolidin-4-ylidene]methyl}- thymine (6), and 1-[(E)-[3-(hydroxymethyl)-2-methylisoxazolidin-5-ylidene]methyl}thymine (7) is described. The first compound can be regarded as a N,O-analogue of Entecavir and DMDC, which contains thymine as a nucleobase. The key allenic nucleobase was prepared in good yields starting from 2,3-dibromopropene. The subsequent 1,3-dipolar cycloaddition proceeded with good site selectivity to give 5 and regioisomeric nucleosides 6 and 7. ((c) Wiley-VCH Verlag GmbH & Co.

引用

页码：1517 / 1521

页数：5

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