A novel polymer supported approach to nucleoside modification

被引：26

作者：

Bae, Suyeal ^{[1
]}

Lakshman, Mahesh K. ^{[1
]}

机构：

[1] CUNY City Coll, New York, NY 10031 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 10期

关键词：

D O I：

10.1021/jo702558n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Polymer-supported O-6-(benzotriazol-1-yl)inosine derivatives (Pol-I and Pol-dI) have been synthesized reasonably effectively via reaction of nucleoside phosphonium salts with polymer-linked HOBt (Pol-HOBt). In constast to solution chemistry, use of polymer-supported BOP (Pol-BOP) did not lead to efficient nucleoside loading. Presence of the nucleosides on the support could be readily detected by MAS NMR. Exposure of the polymer-supported nucleosides, Pol-I and Pol-dI, to alcohol, phenol, thiol and amine nucleophiles caused cleavage from the support leading directly to the C-6 modified nucleoside analogues. To our knowledge, these are the first examples of the application of such technology for nucleoside modification. Where possible, results of reactions with the polymer-supported nucleosides are compared to those from solution chemistry, providing insight into the differences between the two techniques. These new polymer-supported nucleosides can be conveniently utilized for diversity-oriented synthesis.

引用

页码：3707 / 3713

页数：7

共 44 条

[31] UTILITY OF PURINYL RADICALS IN THE SYNTHESIS OF BASE-MODIFIED NUCLEOSIDES AND ALKYLPURINES - 6-AMINO GROUP REPLACEMENT BY H, CL, BR, AND I [J].