Solid Phase Synthesis of Nucleobase and Ribose Modified Inosine Nucleoside Analogues

Abstract

The synthesis and the use of new N-1-dinitrophenyl-inosine based solid support is reported. The support, which binds the nucleoside by a 5 ′-O-monomethoxytrityl function, reacting with N-nucleophiles allowed the synthesis of a small library of N-1 alkylated inosine and AICAR derivatives. Moreover, the obtained supports, after the cleavage of the 2 ′ -3 ′ ribose bond, furnished a set of new N-1 alkylated-2 ′ -3 ′ -secoinosine derivatives in high yields.

Keywords:

• N-1-Dinitrophenyl-inosine based solid support
• N-nucleophiles
• 2′
• -3′-seconucleosides

Notes

^aStarting from resin 2.

^b400 MHz, (CD₃OD) significative protons at ppm.

^cStarting from resin 3.