Synthesis of Nucleoside Mono-, Di-, and Triphosphoramidates from Solid-Phase <i>cyclo</i>Saligenyl Phosphitylating Reagents
作者:Yousef Ahmadibeni、Rakesh K. Tiwari、Gongqin Sun、Keykavous Parang
DOI:10.1021/ol900320r
日期:2009.5.21
Subsequent reduction with borane solution produced polymer-bound 2-hydroxybenzyl alcohol. The reaction of immobilized 2-hydroxybenzyl alcohol with appropriate phosphitylating reagents yielded solid-phase cycloSaligenyl mono-, di-, and triphosphitylating reagents, which were reacted with unprotected nucleosides, followed by iodine oxidation, deprotection of cyanoethoxy groups, and the basic cleavage, respectively
在碳酸钾的存在下,氯甲基聚苯乙烯树脂与 5-羟基水杨醛反应,得到聚合物结合的 2-羟基苯甲醛。随后用硼烷溶液还原产生聚合物结合的 2-羟基苯甲醇。固定化的 2-羟基苯甲醇与适当的亚磷酸酯化试剂反应生成固相环水杨基单-、二-和三亚磷酸酯化试剂,其与未保护的核苷反应,随后碘氧化、氰乙氧基脱保护和碱性裂解,分别以52-73% 的总产率提供 5'- O-核苷单-、二-和三氨基磷酸酯。