Sonogashira reactions of α- and β-1-ethynyl-2-deoxyribosides: synthesis of acetylene-extended C-nucleosides

被引：12

作者：

Bobula, Tomas ^{[2
]}

Hocek, Michal ^{[1
]}

Kotora, Martin ^{[1
,2
]}

机构：

[1] Acad Sci Czech Republ, Inst Organ Chem & Biochem, CR-16610 Prague 6, Czech Republic

[2] Charles Univ Prague, Fac Sci, Dept Organ & Nucl Chem, Prague 12843 2, Czech Republic

来源：

TETRAHEDRON | 2010年 / 66卷 / 02期

关键词：

Alkynes; C-nucleosides; Aryl halides; Cross-coupling reactions; UNNATURAL BASE-PAIR; CONVENIENT SYNTHESIS; ALKYL-HALIDES; DNA; POLYMERIZATION; ARYLGLYCOSIDES; OPTIMIZATION; EXPANSION; CATALYSTS; SCAFFOLD;

D O I：

10.1016/j.tet.2009.11.030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An improved practical protocol for the synthesis of both anomers of 1-ethynyl-2-deoxiribosides 1 was developed. The Sonogashira coupling of ethynyldeoxyribosides 1 with various aryl- and heteroaryl halides was carried out under various conditions. It was found that the use of copper-free coupling protocols could reduce the oxidative dimerisation in favour of arylalkynyldeoxyriboside formation. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：530 / 536

页数：7

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