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

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

Journal Name: Letters in Organic Chemistry

Volume 8 , Issue 5 , 2011

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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.

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

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Article Details

VOLUME: 8
ISSUE: 5
Year: 2011
Page: [309 - 314]
Pages: 6
DOI: 10.2174/157017811795685027
Price: $58

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