A Solid Phase Reagent for the Capture Phosphorylation of Carbohydrates and Nucleosides

• Published in: Organic letters Vol. 3; no. 2; pp. 307 - 309
• Main Authors: Parang, Keykavous, Fournier, Eric J.-L, Hindsgaul, Ole
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 25-01-2001
• Subjects: Indicators and Reagents; Nucleotides - chemical synthesis; Phosphines; Phosphorylation; Polystyrenes - chemical synthesis; Sugar Phosphates - chemical synthesis
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/ol0069498

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.