Zhang Zhibo, Wauchope Orrette R, Seley-Radtke Katherine L
Department of Chemistry and Biochemistry, University of Maryland, Baltimore Co.,, Baltimore, MD 21250.
Tetrahedron. 2008 Nov 24;64(48):10791-10797. doi: 10.1016/j.tet.2008.09.011.
During the synthetic pursuit of guanosine (triG) and xanthosine (triX) tricyclic nucleosides analogues, an interesting side product was discovered. In an effort to uncover the mechanistic factors leading to this result, a series of reaction conditions were investigated. It was found that by varying the conditions, the appearance of the side product could be controlled. In addition, the yield of the desired products could be manipulated to afford either a 50:50 mix of both triG and triX, or a majority of one or the other. To demonstrate the broad utility of the method, it was also adapted to the synthesis of guanosine and xanthosine from 5-amino-1-beta-D-ribofuranosyl-4-imidazolecarboxyamide (AICAR). The mechanistic details surrounding the synthetic efforts are reported herein.
在合成鸟苷（triG）和黄苷（triX）三环核苷类似物的过程中，发现了一种有趣的副产物。为了揭示导致这一结果的机制因素，研究了一系列反应条件。结果发现，通过改变条件，可以控制副产物的出现。此外，所需产物的产率可以进行调控，以得到triG和triX各占50:50的混合物，或者其中一种占多数的产物。为了证明该方法的广泛实用性，它还被应用于从5-氨基-1-β-D-呋喃核糖基-4-咪唑甲酰胺（AICAR）合成鸟苷和黄苷。本文报道了围绕合成工作的机制细节。
