93496-28-7Relevant academic research and scientific papers
PHOTO-OXYGENATION OF GLYCOSYLFURANS. REARRANGEMENT OF C-GLYCOSYL INTO O-GLYCOSYL DERIVATIVES
Aparicio, F. J. Lopez,Sastre, J. A. Lopez,Garcia, J. Isac,Diaz, R. Robles
, p. 19 - 28 (2007/10/02)
Photo-oxygenation of 3-ethoxycarbonyl-5-(2,3-O-isopropylidene-β-D-erythrofuranosyl)-2-methylfuran and 3-hydroxymethyl-5-(2,3-O-isopropylidene-β-D-erythrofuranosyl)-2-methylfuran yields the corresponding endo-peroxydes which rearrange at room temperature into the O-glycosyl derivatives ethyl 2,3-O-isopropylidene-β-D-erythrofuranosyl 2-acetylfumarate and 2,3-O-isopropylidene-β-D-erythrofuranosyl 3-acetyl-3-hydroxymethylacrylate, respectively.The endo-peroxides can be reduced without rearrangement, yielding C-glycosyl derivatives.Alcoholysis of the O-glycosyl derivatives yields 2,3-O-isopropylidene-D-erythrose, dialkyl 2-acetyl-3-alkoxysuccinates, 4-ethoxycarbonyl-5-methoxy-5-methyl-2-oxo-2,5-dihydrofuran and 4-hydroxymethyl-5-methoxy-5-methyl-2-oxo-2,5-dihydrofuran.
