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
收藏
页码：1517 / 1521
页数：5
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