A P(V)鈥揘 Activation Strategy for the Synthesis of Nucleoside Polyphosphates

详细信息    查看全文

• 作者：Qi Sun ; Shanshan Gong ; Jian Sun ; Si Liu ; Qiang Xiao ; Shouzhi Pu
• 刊名：Journal of Organic Chemistry
• 出版年：2013
• 出版时间：September 6, 2013
• 年：2013
• 卷：78
• 期：17
• 页码：8417-8426
• 全文大小：544K
• 年卷期：v.78,no.17(September 6, 2013)
• ISSN：1520-6904

文摘

A general and high-yielding synthesis of nucleoside 5鈥?triphosphates (NTPs) and nucleoside 5鈥?diphosphates (NDPs) from protected nucleoside 5鈥?phosphoropiperidates promoted by 4,5-dicyanoimidazole (DCI) has been developed. ³¹P NMR tracing experiments showed that the sequential deprotection and coupling reactions were exceptionally clean. The phosphoropiperidate exhibited superior reactivity to the conventional phosphoromorpholidate toward DCI-promoted NTP/NDP synthesis. The experimental results suggested that the mechanism of DCI activation could be distinctive for NTP and NDP synthesis, depending on the different nucleophilicity of pyrophosphate and phosphate.