Solid-phase reagents for selective monophosphorylation of carbohydrates and nucleosides

Yousef Ahmadibeni, Keykavous Parang

Research output: Contribution to journalArticle

Abstract

(Chemical Equation Presented) Two classes of aminomethyl polystyrene resin-bound linkers of p-acetoxybenzyl alcohol were subjected to reactions with 2-cyanoethyl N,N-diisopropylchlorophosphoramidite to produce the corresponding polymer-bound phosphitylating reagents. These were reacted with a number of unprotected nucleosides and carbohydrates in the presence of 1H-tetrazole. Oxidation with tert-butyl hydroperoxide followed by removal of the cyanoethoxy group with 1,8-diazabicyclo-[5.4.0]undec-7-ene afforded the corresponding polymerbound phosphate diesters. Acidic cleavage of the p-acetoxybenzyl alcohol linker yielded monophosphorylated products with high regioselectivity and trapped linkers on the resins that can be reused.

Original languageEnglish (US)
Pages (from-to)1100-1103
Number of pages4
JournalJournal of Organic Chemistry
Volume70
Issue number3
DOIs
StatePublished - Feb 4 2005
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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