title: Photochemistry on soluble polymer supports: synthesis of nucleosides.
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.
authors.affiliation: Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario M3J 1P3, Canada.
authors.forename: Jian-Hua
authors.initials: JH
authors.lastname: Zhong
authors.forename: Alex
authors.initials: A
authors.lastname: Fishman
authors.forename: Edward
authors.initials: E
authors.lastname: Lee-Ruff
mesh_terms: D003503:Cyclobutanes / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D010777:Photochemistry; D011092:Polyethylene Glycols / Q000737:chemistry; D011108:Polymers / Q000737:chemistry*; D012263:Ribonucleosides / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D003503:Cyclobutanes; D007659:Ketones; D009705:Nucleosides; D011108:Polymers; D012263:Ribonucleosides; D011092:Polyethylene Glycols