Synthesis of nucleoside mono-, di-, and triphosphoramidates from solid-phase cyc/osaligenyl phosphitylating reagents

Yousef Ahmadibeni, Rakesh K. Tiwari, Gongqin Sun, Keykavous Parang

Research output: Contribution to journalArticle

Abstract

Chloromethyl polystyrene resin was reacted with 5-hydroxysalicylaldehyde in the presence of potassium carbonate to afford polymer-bound 2-hydroxybenzaldehyde. Subsequent reduction with borane solution produced polymer-bound 2-hydroxybenzyl alcohol. The reaction of immobilized 2-hydroxybenzyl alcohol with appropriate phosphitylating reagents yielded solid-phase cyc/oSaligenyl mono-, di-, and triphosphitylating reagents, which were reacted with unprotected nucleosides, followed by iodine oxidation, deprotection of cyanoethoxy groups, and the basic cleavage, respectively, to afford 5′-O-nucleoside mono-, di-, and triphosphoramidates in 52-73% overall yield.

Original languageEnglish (US)
Pages (from-to)2157-2160
Number of pages4
JournalOrganic Letters
Volume11
Issue number10
DOIs
StatePublished - May 21 2009
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

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