嘌呤核苷和嘧啶核苷的一锅法醚化反应。
One-pot etherification of purine nucleosides and pyrimidines.
机构信息
Department of Chemistry, The City College and The City University of New York, 160 Convent Avenue, New York, New York 10031-9198, USA.
出版信息
Org Lett. 2010 Oct 15;12(20):4478-81. doi: 10.1021/ol101655h.
Abstract
A one-pot synthesis of ethers derived from inosine, guanosine, 2'-deoxyguanosine, and pyrimidinones is described. Exposure of the heterocycle to 1H-benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and Cs(2)CO(3) produces a reactive intermediate, which is converted to the desired ether by subsequent addition of an appropriate alcohol or phenol and Cs(2)CO(3). Although rapid formation of HMPA from BOP can occur in the presence of an alcohol and base, as demonstrated by the reaction with methanol, under appropriate conditions these heteroaryl ethers can be efficiently synthesized.
摘要
描述了一种由肌苷、鸟苷、2'-脱氧鸟苷和嘧啶酮衍生的醚的一锅合成方法。将杂环暴露于 1H-苯并三唑-1-基氧基-三（二甲氨基）膦六氟磷酸盐（BOP）和 Cs（2）CO（3）下会产生一个反应性中间体，通过随后加入适当的醇或酚和 Cs（2）CO（3），将其转化为所需的醚。尽管 BOP 与醇和碱共存时会迅速形成 HMPA，如与甲醇的反应所示，但在适当的条件下，这些杂芳基醚可以有效地合成。
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