Photochemistry on soluble polymer supports: synthesis of nucleosides.
[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.
Zhong
Jian-Hua
JH
Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario M3J 1P3, Canada.
Fishman
Alex
A
Lee-Ruff
Edward
E
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
D003503:Cyclobutanes; D007659:Ketones; D009705:Nucleosides; D011108:Polymers; D012263:Ribonucleosides; D011092:Polyethylene Glycols