Synthesis of bitriazolyl nucleosides and unexpectedly different reactivity of azidotriazole nucleoside isomers in the Huisgen reaction
Synthesis of bitriazolyl nucleosides and unexpectedly different reactivity of azidotriazole nucleoside isomers in the Huisgen reaction
复制标题
双三唑基核苷的合成以及叠氮三唑核苷异构体在胡伊斯根反应中的意外不同反应性
DOI：
10.1039/b703420b
复制
发表时间：
2007-01-01
影响因子：
3.2
通讯作者：
Peng, Ling
中科院分区：
文献类型：
--
作者：
Xia, Yi;Li, Wei;Peng, Ling
以3-叠氮三唑核苷(1)为起始原料，通过Huisgen反应合成了新型双氮唑核苷。令人惊讶的是，它的异构体，5-氮杂三唑核苷（1'）不能有效地产生相应的Huisgen反应产物，因为它在Cu(II)-抗坏血酸存在下迅速还原为胺。这两种异构体在Cu(II)-抗坏血酸介导的反应中反应活性的显著差异主要是由于叠氮基团和核糖基基团的相对位置不同导致它们的电子性质和位阻的差异。
Novel bitriazolyl nucleosides were synthesized via the Huisgen reaction, starting with 3-azidotriazole nucleoside (1). Surprisingly, its isomer, 5-azidotriazole nucleoside (1') did not yield the corresponding Huisgen reaction products efficiently because it was rapidly reduced to amine in the presence of Cu(II)-ascorbate. The significant differences between the reactivity of these two isomers in Cu(II)-ascorbate mediated reactions are mainly due to differences in their electronic properties and steric congestion as a result of different relative positions of the azido and the ribosyl moieties.