T. Maeda
Sep 1, 1967
Citations
0
Influential Citations
14
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
The acetonation reaction of L-sorbose with acetone dimethyl ketal was investigated. The products and the yields were greatly influenced by the reaction conditions. The reaction at 45°C gave 1, 3 : 4, 6-di-O-isopropylidene-β- (VIIa), 1, 2 : 4, 6-di-O-isopropylidene-α- (Va) and 2, 3 : 4, 6-di-O-isopropylidene-α-L-sorbofuranose (IVa) and the β-anomer of Va (VIa). At the refluxing temperature, the reaction afforded IVa and the 2-O-methyl derivative of VIIa (VIIe), while at room temperature it yielded 1, 2 : 3, 4-di-O-isopropylidene-α-L-sorbopyranose (VIIIa), 1, 2 : 4, 5-di-O-isopropylidene-α-L-sorbopyranose (IXa), and 5-O-α-methoxyisopropyl-1, 2 : 3, 4-di-O-isopropylidene-α-L-sorbopyranose (VIIIc).