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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
