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Photochemistry on soluble polymer supports: synthesis of nucleosides
Jian-Hua Zhong1, Alex Fishman, Edward Lee-Ruff
1Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario M3J 1P3, Canada.
Organic Letters
|December 6, 2002
Abstract:
[reaction: see text] A new soluble polymer support synthesis of nucleosides is described. The photochemical ring expansion of cyclobutanones in the presence of poly(ethylene glycol) (PEG) results in polymer-supported ribosides. These photoadducts can be cleaved from the polymer under Vorbrüggen coupling conditions with TMS-protected purines and pyrimidines to give ribonucleosides. The method has been extended to include modified PEGs with dendritic end-groups in order to improve the loading levels for these coupling reactions.