Solid-phase synthesis of symmetrical 5′,5′-dinucleoside mono-, di-, tri-, and tetraphosphodiesters
Solid-phase synthesis of symmetrical 5′,5′-dinucleoside mono-, di-, tri-, and tetraphosphodiesters
复制标题
DOI：
10.1021/ol7018778
复制
发表时间：
2007-10-25
期刊：
影响因子：
5.2
通讯作者：
Parang, Keykavous
中科院分区：
文献类型：
--
作者：
Ahmadibeni, Yousef;Parang, Keykavous
[图形]四类磷酸化试剂与氨基甲基聚苯乙烯树脂结合的对乙酰氧基苄基醇反应，得到相应的聚合物结合的单、二、三和四磷酸化试剂。固相试剂在5-（乙基硫）- 1h -四唑的存在下与无保护的核苷（如胸腺嘧啶、腺苷、3'-叠氮-3'-脱氧胸腺嘧啶、胞苷或肌苷）反应。聚合结合的核苷分别经过叔丁基过氧化氢氧化、DBU对氰乙氧基脱保护和酸性裂解，得到5′、5′-二核苷单、二、三和四磷酸二酯，产率为59-78%。
[GRAPHICS]Four classes of phosphitylating reagents were subjected to reactions with aminomethyl polystyrene resin-bound p-acetoxybenzyl alcohol to yield the corresponding polymer-bound mono-, di-, tri-, and tetraphosphitylating reagents. The solid-phase reagents were reacted with unprotected nucleosides (e.g., thymidine, adenosine, 3'-azido-3'-deoxythymidine, cytidine, or inosine) in the presence of 5-(ethylthio)-1H-tetrazole. Polymerbound nucleosides underwent oxidation with tert-butyl hydroperoxide, deprotection of cyanoethoxy groups with DBU, and the acidic cleavage, respectively, to afford 5',5'-dinucleoside mono-, di-, tri-, and tetraphosphodiesters in 59-78% yield.