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