Dye-Sensitized Photooxygenation of 2,5-Bis(glycosyl)furans

Title: Dye-Sensitized Photooxygenation of 2,5-Bis(glycosyl)furans

Volume: 8 Issue: 5

Author(s): Flavio Cermola, Maria R. Iesce, Anna Astarita and Monica Passananti

Affiliation:

Keywords: [4+2]-Cycloaddition, endoperoxides, glycosyl furans, glycosides, photooxygenation, singlet oxygen, thermal rearrangement, rearrangement, dichloromethane, disaccharidic systems

Abstract: The dye-sensitized photooxygenation of 2,5-bis(glycosyl)furans followed by warming up to r.t. provides 1,1- linked disaccharides separated by a functionalized spacer. Asymmetrical disubstituted glycosyl furans give the corresponding Bayer-Villiger type-rearranged products in a molar ratio depending on the sugars and the protecting groups. The migratory aptitudes have been rationalized by both theoretical calculations and experimental data. The 1,1- disaccharides obtained are new sugar derivatives structurally related to some mimetics of Sialyl Lewis X.

Cite this article as:

Cermola Flavio, R. Iesce Maria, Astarita Anna and Passananti Monica, Dye-Sensitized Photooxygenation of 2,5-Bis(glycosyl)furans, Letters in Organic Chemistry 2011; 8 (5) . https://dx.doi.org/10.2174/157017811795685027