Expeditious convergent procedure for the preparation of bis(POC) prodrugs of new (E)-4-phosphono-but-2-en-1-yl nucleosides

详细信息    查看全文

• 作者：Auré ; lien Montagu^a ; Ugo Pradé ; re^a ; Vincent Roy^a ; Steven P. Nolan^b ; Luigi A. Agrofoglio^a ; ^{luigi.agrofoglio@univ-orleans.fr"" rel=""nofollow}
• 关键词：Acyclonucleoside phosphonates ; Prodrug ; Olefin cross metathesis
• 刊名：Tetrahedron
• 出版年：2011
• 出版时间：22 July 2011
• 年：2011
• 卷：67
• 期：29
• 页码：5319-5328
• 全文大小：880 K

文摘

A series of unsaturated acyclonucleoside bis(POC) prodrugs of E configuration were synthesized through an expeditious, highly efficient and stereoselective one-step procedure from corresponding bis(POC)allylphosphonate through Ru catalyzed cross-coupling metathesis reaction. The [RuCl₂(PCy₃)(SIPr)(Indenylidene)] and [RuCl₂(PCy₃)(IMes)(benzylidene)] catalysts were employed; the unsaturated ANP were used bore C5-halovinyl uracil, C5-dihalovinyluracil or furanopyrimidine motifs. The chemical cleavage of biolabile (POC) group is a useful pathway to acid phosphonate derivatives.