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

Yousef Ahmadibeni; Keykavous Parang

doi:10.1021/ol050385w

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

Yousef Ahmadibeni·Keykavous Parang

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Abstract

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.

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Carbohydrates Indicators and Reagents Nucleosides Nucleotides Polymers Ribose Stereoisomerism Journal Article Research Support, N.I.H., Extramural Research Support, U.S. Gov't, P.H.S.

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Yousef Ahmadibeni, Keykavous Parang. 2005-05-12. Polymer-bound oxathiaphospholane: a solid-phase reagent for regioselective monothiophosphorylation and monophosphorylation of unprotected nucleosides and carbohydrates.. https://doi.org/10.1021/ol050385w

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