Zhong Minghong, Nowak Ireneusz, Robins Morris J
Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602-5700, USA.
Org Lett. 2005 Oct 13;7(21):4601-3. doi: 10.1021/ol051573p.
[reaction: see text] Regioselective control of glycosylation of purines at N9 (versus N7) has been a continuing challenge. We now report Lewis acid catalyzed regiospecific glycosylations of 6-(2-alkylimidazol-1-yl)purines at N9. The 6-(2-alkyl)imidazole moiety also functions as a versatile leaving group that can be replaced by nucleophiles (S(N)Ar) and aryl groups (Suzuki cross-coupling).
[反应：见正文]嘌呤在N9位（相对于N7位）糖基化的区域选择性控制一直是一个持续存在的挑战。我们现在报道了在Lewis酸催化下，6-(2-烷基咪唑-1-基)嘌呤在N9位的区域特异性糖基化反应。6-(2-烷基)咪唑部分还作为一种通用的离去基团，可以被亲核试剂（亲核芳香取代反应）和芳基（铃木交叉偶联反应）取代。
