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

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.