Solid-phase synthesis of dinucleoside and nucleoside-carbohydrate phosphodiesters and thiophosphodiesters

Yousef Ahmadibeni, Keykavous Parang

Research output: Contribution to journalArticlepeer-review

Abstract

Unprotected nucleosides (ROH) were reacted with two polymers bound to N,N-diisopropylamino-1,3,2-oxathiaphospholane in the presence of 1H-terazole. Oxidation with tert-butyl hydroperoxide or sulfurization with Beaucage's reagent, followed by the 1,3,2-oxathiaphospholane ring opening with unprotected nucleosides or carbohydrates (R′OH) in the presence of DBU, afforded nucleoside-(5′-5′)-nucleoside or nucleoside-carbohydrate phosphodiester and thiophosphodiester derivatives through the elimination of polymer-bound ethylene episulfide. This strategy offers the advantages of facile isolation of final products and monosubstitution of unprotected nucleosides and carbohydrates.

Original languageEnglish (US)
Pages (from-to)6693-6696
Number of pages4
JournalJournal of Organic Chemistry
Volume71
Issue number17
DOIs
StatePublished - Aug 18 2006
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Solid-phase synthesis of dinucleoside and nucleoside-carbohydrate phosphodiesters and thiophosphodiesters'. Together they form a unique fingerprint.

Cite this