Herein, we report the synthesis and the use of new N-1-dinitrophenyi-inosine based solid supports, in which the C-2 of the purine base is strongly activated toward the attack of N-nucleophiles. The synthesized supports, binding the nucleoside by a 5'-O-monomethoxytrityl function, have been used to accomplish the synthesis of a small library of N-1 alkylated inosine and AICAR derivatives. In addition, cleavage of the 2'-3' ribose bond of N-1 alkylated inosine derivatives anchored to the supports allowed to prepare a new set of N-1 alkylated-2',3'-secoinosine derivatives in high yields. (c) 2006 Elsevier Ltd. All rights reserved.
Synthesis of N-1 and ribose modified inosine analogues on solid support / Oliviero, Giorgia; Amato, Jussara; Borbone, Nicola; D'Errico, Stefano; Piccialli, Gennaro; Mayol, Luciano. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 48:3(2007), pp. 397-400. [10.1016/j.tetlet.2006.11.085]
Synthesis of N-1 and ribose modified inosine analogues on solid support.
OLIVIERO, GIORGIA;AMATO, JUSSARA;BORBONE, NICOLA;D'ERRICO, STEFANO;PICCIALLI, GENNARO;MAYOL, LUCIANO
2007
Abstract
Herein, we report the synthesis and the use of new N-1-dinitrophenyi-inosine based solid supports, in which the C-2 of the purine base is strongly activated toward the attack of N-nucleophiles. The synthesized supports, binding the nucleoside by a 5'-O-monomethoxytrityl function, have been used to accomplish the synthesis of a small library of N-1 alkylated inosine and AICAR derivatives. In addition, cleavage of the 2'-3' ribose bond of N-1 alkylated inosine derivatives anchored to the supports allowed to prepare a new set of N-1 alkylated-2',3'-secoinosine derivatives in high yields. (c) 2006 Elsevier Ltd. All rights reserved.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
