The First Dye-sensitized Photooxygenation of 2-(C-glycosyl)furans. One-Pot Stereoselective Approach to New Carbohydrate Derivatives

Title: The First Dye-sensitized Photooxygenation of 2-(C-glycosyl)furans. One-Pot Stereoselective Approach to New Carbohydrate Derivatives

Volume: 1 Issue: 3

Author(s): Flavio Cermola, M. Rosaria Iesce and Stefania Montella

Affiliation:

Keywords: photooxygenation, 2-(c-glucopyranosyl)furans, o-glucopyranosides, c-glucopyranosides, furan-based synthesis, cis-1,4-dioxo-2-alkenyl glucopyranosides

Abstract: The singlet oxygen oxygenation of 2-(α-C-glucopyranosyl)furans 1 leads readily and diastereoselectivity to the corresponding endoperoxides 2 whose fate can be controlled. Compounds 2 thermally rearrange into cis-dicarbonyl-α-O-glucosides 3 while by reduction they afford the cis-C-analogs 5. The latter readily convert to trans-8, which by silica gel chromatography tautomerize into β-anomers 9.

Cite this article as:

Cermola Flavio, Iesce Rosaria M. and Montella Stefania, The First Dye-sensitized Photooxygenation of 2-(C-glycosyl)furans. One-Pot Stereoselective Approach to New Carbohydrate Derivatives, Letters in Organic Chemistry 2004; 1 (3) . https://dx.doi.org/10.2174/1570178043400839