Synthesis of Ribooligonucleotides Using the 4-Methoxybenzyl Group as a New Protecting Group for the 2'-Hydroxyl Group

Article abstract of DOI:10.1021/jo00175a010

The 4-methoxybenzyl group was introduced to protect the 2'-hydroxyl group of uridine, cytidine, and N²-benzoylguanosine by treatment of 2',3'-O-(dibutylstannylene)uridine or NaH-treated nucleosides with 4-methoxybenzyl bromide.The 2'-O-(4-methoxybenzyl)nucleosides can be used as useful starting materials for the synthesis of 3',5'-linked ribooligonucleotides.The 4-methoxybenzyl group was removed rapidly from the ribooligonucleotides by treatment with triphenylmethyl fluoroborate, and the completely deblocked ribooligonucleotides were characterized by enzymatic hydrolysis.