Synthesis of Bis(5-chloro-8-quinolyl) Nucleoside 5'-Phosphates in Oligoribonucleotide Synthesis by the Phosphotriester Approach

Article abstract of DOI:10.1021/jo00146a022

A new phosphorylating agent, bis(5-chloro-8-quinolyl) phosphate was found to be a useful agent for the phosphorylation of the 5'-hydroxyl group of unprotected nucleosides.This agent smoothly reacts with 3',5',-unprotected nucleosides in the presence of 8-quinolinesulfonyl tetrazolide (QS-t) to give the corresponding bis(5-chloro-8-quinolyl) nucleoside 5'-phosphates in good yields without 3'-mono- and 3',5'-diphosphorylated products.They are key intermediates for the synthesis of oligoribonucleotides bearing 5'-terminal phosphate.Zinc chloride can be used as an effective and mild agent for removal of 5-chloro-8-quinolyl group.