Application of a solid-phase β-triphosphitylating reagent in the synthesis of nucleoside β-triphosphates

Yousef Ahmadibeni, Keykavous Parang

Research output: Contribution to journalArticlepeer-review

Abstract

A β-triphosphitylating reagent was subjected to reaction with aminomethyl polystyrene resin-bound p-acetoxybenzyl alcohol to yield the corresponding polymer-bound β-triphosphitylating reagent. The solid-phase reagent was reacted with unprotected nucleosides (e.g., 3′-azido-3′- deoxythymidine, cytidine, thymidine, uridine, inosine, or adenosine) in the presence of 1H-tetrazole. Polymer-bound nucleosides underwent oxidation with t-butyl hydroperoxide, deprotection of cyanoethoxy groups with DBU, and the acidic cleavage, respectively, to afford only monosubstituted 5′-O-β-triphosphorylated nucleosides.

Original languageEnglish (US)
Pages (from-to)5837-5839
Number of pages3
JournalJournal of Organic Chemistry
Volume71
Issue number15
DOIs
StatePublished - Jul 21 2006
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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