Developing an efficient route to the synthesis of nucleoside 1-alkynylphosphonates

被引:10
作者
Meurillon, Maia [1 ]
Gallier, Franck [1 ]
Peyrottes, Suzanne [1 ]
Perigaud, Christian [1 ]
机构
[1] Univ Montpellier 2, CNRS,UMR 5247,UM2, IBMM, Equipe Nucleosides & Effecteurs Phosphoryles,UM1, F-34095 Montpellier 05, France
关键词
Nucleotide analogue; 1-Alkynylphosphonate; Sugar phosphonate; 1,1-DIBROMO-1-ALKENES; DERIVATIVES; ANALOGS;
D O I
10.1016/j.tet.2009.05.064
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of ribonucleoside 1-alkynylphosphonates have been synthesized using a palladium-catalyzed phosphonylation of terminal 1,1-dibromo-1-alkene nucleosidic derivatives and high selectivity for product distribution was observed during this step. Both nucleosidic and osidic pathways were explored and the corresponding optimization study is reported herein. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6039 / 6046
页数:8
相关论文
共 20 条
[1]  
CHATTHA MS, 1971, J ORG CHEM, V36, P2719
[2]  
Corey E.J., 1972, TETRAHEDRON LETT, V13, P3769
[3]   Ex-chiral-pool synthesis of β-hydroxyphosphonate nucleoside analogues [J].
Gallier, Franck ;
Peyrottes, Suzanne ;
Perigaud, Christian .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (06) :925-933
[5]   WITTIG SYNTHESES OF DIHALO-OLEFINS BY REACTION OF CARBONYL-COMPOUNDS WITH POLYMER-SUPPORTED PHOSPHINES AND CARBON TETRAHALIDES [J].
HODGE, P ;
KHOSHDEL, E .
REACTIVE POLYMERS, 1985, 3 (02) :143-150
[6]  
Iorga B, 2000, EUR J ORG CHEM, V2000, P3103
[7]   Oxidative cleavage of ribofuranose 5-(α-hydroxyphosphonates):: a route to erythrofuranose-based nucleoside phosphonic acids [J].
Kralikova, Sarka ;
Budesinsky, Milos ;
Tomeckova, Ivana ;
Rosenberg, Ivan .
TETRAHEDRON, 2006, 62 (41) :9742-9750
[8]   3′-deoxy-3′-C-trifluoromethyl nucleosides:: Synthesis and antiviral evaluation [J].
Lavaire, S ;
Plantier-Royon, R ;
Portella, C ;
de Monte, M ;
Kirn, A ;
Aubertin, AM .
NUCLEOSIDES & NUCLEOTIDES, 1998, 17 (12) :2267-2280
[9]  
LECLERCLE D, 2007, SYNTHETIC COMMUN, V37, P1301
[10]   A new one-pot synthesis of alkynylphosphonates [J].
Lera, M ;
Hayes, CJ .
ORGANIC LETTERS, 2000, 2 (24) :3873-3875