47001-46-7Relevant academic research and scientific papers
SiO2-supported CeCl3·7H2O-NaI Lewis acid promoter: Investigation into the Garcia Gonzalez reaction in solvent-free conditions
Bartoli, Giuseppe,Fernandez-Bolanos, Jose G.,Di Antonio, Giustino,Foglia, Gioia,Giuli, Sandra,Gunnella, Roberto,Mancinelli, Michele,Marcantoni, Enrico,Paoletti, Melissa
, p. 6029 - 6036 (2007)
(Chemical Equation Presented) The Knoevenagel condensation of aldose sugars with β-dicarbonyl compounds produces furan derivatives having polyhydroxyalkylated alkyl side chains; this reaction is known as the Garcia Gonzalez reaction. Despite the fact that
PHOTO-OXYGENATION OF POLYHYDROXYALKYLFURANS: REARRANGEMENT OF O-ACETYL DERIVATIVES
Aparicio, F. J. Lopez,Diaz, R. Robles,Garcia, J. Isac,Calvo-Flores, Garcia
, p. 235 - 248 (1986)
The photo-oxygenation of ethyl 2-methyl-5-(1,2,3,4-tetra-O-acetyl-D-lyxo-tetritol-1-yl)-3-furoate, ethyl 2-methyl-5-(1,2,3,4-tetra-O-acetyl-D-arabino-tetritol-1-yl)-3-furoate, 3-acetyl-2-methyl-5-(1,2,3,4-tetra-O-acetyl-D-arabino-tetritol-1-yl)furan, and ethyl 5-(1,4-di-O-acetyl-2,3-O-isopropylidene-D-lyxo-tetritol-1-yl)-2-methyl-3-furoate yielded the corresponding 1,4-endo-peroxides (3a-3d as pairs of diastereomers).Each diastereomer of the pairs 3a and 3d was isolated by fractional crystallisation.The rearrangement of the endo peroxides at room temperature, by dissolution in CDCl3, yielded the corresponding diepoxides and monoepoxides.The reduction of 3a-3d with methyl sulphide yielded the corresponding γ-diketones, ethyl (E)-2-C-acetyl-5,6,7,8-tetra-O-acetyl-2,3-dideoxy-D-lyxo-oct-2-en-4-ulosonate, ethyl (E)-2-C-acetyl-5,6,7,8-tetra-O-acetyl-2,3-dideoxy-D-arabino-oct-2-en-4-ulosonte, 3-C-acetyl-6,7,8,9-tetra-O-acetyl-1,3,4-trideoxy-D-arabino-non-3-eno-2,5-diulose, and ethyl (E)-2-C-acetyl-5,8-di-O-acetyl-2,3-dideoxy-6,7-O-isopropylidene-D-lyxo-oct-2-en-4-ulosonate, which can isomerise into the correspodig Z isomers.
