262293-07-2Relevant academic research and scientific papers
The synthesis of an O,C-trisaccharide: The O,C-analog of methyl 4'-O-β- D-glucopyranosylgentiobioside
Spak, Stephen J.,Martin, Olivier R.
, p. 217 - 224 (2007/10/03)
The synthesis of an O,C-trisaccharide, namely methyl O-β-D- glucopyranosyl-(1→4)-C-β-D-glucopyranosyl-(1→6)-α-D-glucopyranoside, was achieved in 14 steps by way of the nitro-aldol coupling of hepta-O-acetyl-β- cellobiosylnitromethane and methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-gluco- hexodialdo-1,5-pyranoside, followed by the elaboration of the coupling product. The resulting O,C-trisaccharide constitutes a potential inhibitor of the β-glucanases of the cellulase family. The perbenzylated derivative of cellobiosylnitromethane was also prepared. Both disaccharide-C-glycosides constitute useful starting materials for the preparation of higher mixed O,C- oligosaccharides.
