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

作者：Hogendorf Wouter F J; Verhagen Carlo P; Malta Erik; Goosen Nora; Overkleeft Herman S; Filippov Dmitri V^*; Van der Marel Gij**ert A

来源：Tetrahedron, 2009, 65(50): 10430-10435.

DOI：10.1016/j.tet.2009.10.023

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.

• 出版日期2009-12-12