Polymer-bound oxathiaphospholane: A solid-phase reagent for regioselective monothiophosphorylation and monophosphorylation of unprotected nucleosides and carbohydrates

Yousef Ahmadibeni, Keykavous Parang

Research output: Contribution to journalArticlepeer-review

Abstract

(Chemical Equation Presented) Two polymers bound to N,N-diisopropylamino-1, 3,2-oxathiaphospholane were reacted with unprotected carbohydrates and nucleosides in the presence of 1H-tetrazole, followed by oxidation with tert-butyl hydroperoxide or sulfurization with Beaucage's reagent. The 1,3,2-oxathiaphospholane ring-opening with 3-hydroxypropionitrile, followed by treatment with DBU, afforded the corresponding monophosphate and monothiophosphate derivatives, respectively, through the elimination of polymer-bound ethylene episulfide. Reactions using this strategy offer the advantages of high regioselectivity, monosubstitution, and facile isolation and recovery of products.

Original languageEnglish (US)
Pages (from-to)1955-1958
Number of pages4
JournalOrganic Letters
Volume7
Issue number10
DOIs
StatePublished - May 12 2005
Externally publishedYes

ASJC Scopus subject areas

  • Molecular Medicine

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