Unexpected reductions of glycosyl spacer-armed phthalimides.
An unusual reductive ring-opening reaction in the title compounds, of the phthalimide group with sodium hydride in anhydrous DMF is observed for the first time and the presumed mechanism is described in detail. An unexpected hydrogenation of the phthalimide group was also observed.
Meng
Xiang-Bao
XB
Department of Chemical Biology, School of Pharmaceutical Sciences, National Research Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100083, China.
Li
Hui
H
Lou
Qing-Hua
QH
Cai
Meng-Shen
MS
Li
Zhong-Jun
ZJ
D000812:Anhydrides / Q000737:chemistry; D002240:Carbohydrate Sequence; D004126:Dimethylformamide / Q000737:chemistry; D006865:Hydrogenation; D010084:Oxidation-Reduction; D010797:Phthalimides / Q000737:chemistry*; D012964:Sodium / Q000737:chemistry
D000812:Anhydrides; D010797:Phthalimides; D004126:Dimethylformamide; D012964:Sodium