88885-08-9Relevant academic research and scientific papers
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 (2007/10/03)
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.
Practical synthesis of a C-glycosyl flavonoid via O→C glycoside rearrangement
Kumazawa,Ohki,Ishida,Sato,Onodera,Matsuba
, p. 1379 - 1384 (2007/10/02)
The C-glycosylation of 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl fluoride and 2-acetylphloroglucinol 3,5-bis(alkyl ether) in the presence of boron trifluoride etherate as an activator stereoselectively gave the β-C-glucoside in a good yield via O→C glycos
