A solid phase reagent for the capture phosphorylation of carbohydrates and nucleosides

Keykavous Parang, Eric J L Fournier, Ole Hindsgaul

Research output: Contribution to journalArticle

Abstract

equation presented A 1% cross-linked divinylbenzene-polystyrene copolymer, containing cyanoethoxy N,N-diisopropylamine phosphine was prepared as a phosphitylating agent. The polymer-bound phosphitylated precursor was subjected to reaction with alcohols in the presence of 1H-tetrazole to produce the corresponding polymer-bound phosphite triesters. These were then oxidized with tert-butyl hydroperoxide to give the polymer-bound monophosphate triesters. Removal of cyanoethoxy on the resin with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) followed by basic cleavage of the p-hydroxybenzyl linker products yielded monophosphate derivatives.

Original languageEnglish (US)
Pages (from-to)307-309
Number of pages3
JournalOrganic Letters
Volume3
Issue number2
DOIs
StatePublished - Jan 25 2001
Externally publishedYes

Fingerprint

phosphorylation
Phosphorylation
nucleosides
carbohydrates
Nucleosides
reagents
solid phases
Polymers
phosphine
Carbohydrates
polymers
Phosphites
tert-Butylhydroperoxide
tetrazoles
phosphines
resins
cleavage
polystyrene
copolymers
alcohols

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

A solid phase reagent for the capture phosphorylation of carbohydrates and nucleosides. / Parang, Keykavous; Fournier, Eric J L; Hindsgaul, Ole.

In: Organic Letters, Vol. 3, No. 2, 25.01.2001, p. 307-309.

Research output: Contribution to journalArticle

Parang, Keykavous ; Fournier, Eric J L ; Hindsgaul, Ole. / A solid phase reagent for the capture phosphorylation of carbohydrates and nucleosides. In: Organic Letters. 2001 ; Vol. 3, No. 2. pp. 307-309.
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