Journal of Carbohydrate Chemistry p. 469 - 485 (2011)
Update date:2022-08-03
Topics:
Cumpstey, Ian
Crich, David
A method for photochemical activation of glycosyl donors is presented. Selenoglycosides were activated by single-electron transfer using a photooxidant, N-methylquinolinium hexafluorophosphate, as photosensitizer and a toluene cosolvent as cosensitizer under irradiation at 350 nm. In this way we were able to synthesize glycosides including (1→6)-linked disaccharides. Benzyl ethers and benzoate esters were compatible with these conditions, allowing potentially synthetically useful transformations. The major by-products were due to hydrolysis; the reactions required the presence of oxygen and were run in air.
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