Solid-phase synthesis of symmetrical 5′,5′-dinucleoside mono-, di-, tri-, and tetraphosphodiesters

Yousef Ahmadibeni, Keykavous Parang

Research output: Contribution to journalArticlepeer-review

Abstract

(Chemical Equation Presented) Four classes of phosphitylating reagents were subjected to reactions with aminomethyl polystyrene resin-bound p-acetoxybenzyl alcohol to yield the corresponding polymer-bound mono-, di-, tri-, and tetraphosphitylating reagents. The solid-phase reagents were reacted with unprotected nucleosides (e.g., thymidine, adenosine, 3′-azido-3′- deoxythymidine, cytidine, or inosine) in the presence of 5-(ethylthio)-1H- tetrazole. Polymer-bound nucleosides underwent oxidation with fert-butyl hydroperoxide, deprotection of cyanoethoxy groups with DBU, and the acidic cleavage, respectively, to afford 5′,5′-dinucleoside mono-, di-, tri-, and tetraphosphodiesters in 59-78% yield.

Original languageEnglish (US)
Pages (from-to)4483-4486
Number of pages4
JournalOrganic Letters
Volume9
Issue number22
DOIs
StatePublished - Oct 25 2007
Externally publishedYes

ASJC Scopus subject areas

  • Molecular Medicine

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