Wan Zhao-Kui, Binnun Eva, Wilson Douglas P, Lee Jinbo
Chemical and Screening Sciences, Wyeth Research, 200 Cambridge Park Drive, Cambridge, Massachusetts 02140, USA.
Org Lett. 2005 Dec 22;7(26):5877-80. doi: 10.1021/ol052424+.
[reaction: see text] A highly facile and efficient one-step synthesis of N6-adenosine and N6-2'-deoxyadenosine derivatives has been developed. Treatment of inosine or 2'-deoxyinosine, without protection of sugar hydroxyl groups, with alkyl or arylamines, in the presence of BOP and DIPEA in DMF, led to the formation of N6-adenosine and N6-2'-deoxyadenosine derivatives in good to excellent yields. Carcinogenic polyaromatic hydrocarbon (PAH) N6-2'-deoxyadenosine adduct 10 and a rare DNA constituent 11 were thus synthesized directly from 2'-deoxyinosine both in 98% yield.
[反应：见正文] 已开发出一种高度简便且高效的一步法合成N6-腺苷和N6-2'-脱氧腺苷衍生物的方法。在DMF中，在BOP和N,N-二异丙基乙胺（DIPEA）存在下，用烷基或芳基胺处理未保护糖羟基的肌苷或2'-脱氧肌苷，以良好至优异的产率生成N6-腺苷和N6-2'-脱氧腺苷衍生物。致癌多环芳烃（PAH）N6-2'-脱氧腺苷加合物10和一种罕见的DNA成分11因此都以98%的产率直接由2'-脱氧肌苷合成。
