144152-27-2Relevant articles and documents
Cleavage of the C-C linkage between the sugar and the aglycon in C-glycosylphloroacetophenone, and the NMR spectral characteristics of the resulting di-C-glycosyl compound
Kumazawa,Kimura,Matsuba,Sato,Onodera
, p. 207 - 213 (2001)
The treatment of unprotected mono-C-β-D-glucopyranosylphloroacetophenone with a cation-exchange resin in anhydrous acetonitrile afforded both a phloroacetophenone and a di-C-β-D-glucopyranosylphloroacetophenone. Treatment of an unprotected mono-C-(2-deoxy-β-D-arabino-hexopyranosyl)phloroacetophenone (mono-C-2-deoxy-β-D-glucopyranosylphloroacetophenone) also afforded both the aglycon and di-C-(2-deoxy-β-D-arabino-hexopyranosyl)phloroacetophenone. The reaction mixtures were acetylated, and the structures of the isolated products were determined by NMR spectroscopy. This is the first demonstration of the formation of a di-C-glycosyl compound during the chemical cleavage of the C-C linkage between the sugar and the aglycon in an aryl C-glycosyl derivative.
Concise synthesis of 5-methoxy-6-hydroxy-2-methylchromone-7-O- and 5-hydroxy-2-methylchromone-7-O-rutinosides. Investigation of their cytotoxic activities against several human tumor cell lines
Wu, Baolin,Zhang, Wenpeng,Li, Zhonghua,Gu, Li,Wang, Xin,Wang, Peng George
scheme or table, p. 2265 - 2268 (2011/06/11)
The synthesis of two novel 2-methylchromone-7-O-rutinosides is reported, and the in vitro biological activities of these compounds and their synthetic precursors have been investigated on the basis of their cytotoxicity against several human tumor cell lines. The synthesis features early stage assembly of the acidic labile glycosidic bond between sugar and 2-methylchromone aglycon under phase transfer catalyzed glycosidation conditions, whereas all the other standard glycosylation conditions specific to a wide array of rutinosyl donors bearing different anomeric leaving groups (e.g., SPh, OC(NH)CCl3, Br, OH groups) failed to furnish any detectable products.
