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.

Dye-Sensitized Photooxygenation of 2,5-Bis(glycosyl)furans / Cermola, Flavio; Iesce, MARIA ROSARIA; A., Astarita; Passananti, Monica. - In: LETTERS IN ORGANIC CHEMISTRY. - ISSN 1570-1786. - 8:(2011), pp. 309-314.

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

CERMOLA, FLAVIO;IESCE, MARIA ROSARIA;PASSANANTI, MONICA
2011

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.
2011
Dye-Sensitized Photooxygenation of 2,5-Bis(glycosyl)furans / Cermola, Flavio; Iesce, MARIA ROSARIA; A., Astarita; Passananti, Monica. - In: LETTERS IN ORGANIC CHEMISTRY. - ISSN 1570-1786. - 8:(2011), pp. 309-314.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11588/421645
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