A solid phase reagent for the capture phosphorylation of carbohydrates and nucleosides.
[figure: see text] 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.
Parang
K
K
Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2 Canada. kparang@uri.edu
Fournier
E J
EJ
Hindsgaul
O
O
D007202:Indicators and Reagents; D009711:Nucleotides / Q000138:chemical synthesis*; D010720:Phosphines; D010766:Phosphorylation; D011137:Polystyrenes / Q000138:chemical synthesis*; D013403:Sugar Phosphates / Q000138:chemical synthesis*
D007202:Indicators and Reagents; D009711:Nucleotides; D010720:Phosphines; D011137:Polystyrenes; D013403:Sugar Phosphates; C432006:divinylbenzene-polystyrene copolymer