The synthesis of a menthol derivative of 2-aminopurine as a fluorescent DNA lesion

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• 作者：Wouter F.J. Hogendorf ; Carlo P. Verhagen ; Erik Malta ; Nora Goosen ; Herman S. Overkleeft ; Dmitri V. Filippov ; Gijsbert A. Van der Marel
• 刊名：Tetrahedron
• 出版年：2009
• 出版时间：12 December 2009
• 年：2009
• 卷：65
• 期：50
• 页码：10430-10435
• 全文大小：216 K

文摘

An efficient synthetic route to the phosphoramidite of a menthol functionalized guanosine analog is presented. Two procedures were executed for the key introduction of the 6′-allyl menthyl moiety. Stille vinylation on 6-O-tosylguanosine followed by cross-metathesis using an excess of allyl menthyl ether proved to be less efficient than a Stille coupling on the same tosylate using an advanced menthyl-allyl stannane derivative. Incorporation of the modified nucleoside using the phosphoramidite method into a DNA 50-mer proceeded uneventfully.