The Synthesis of an O,C-Trisaccharide: The O,C-Analog of Methyl 4′-O-β-d-glucopyranosylgentiobioside

✍ Scribed by Stephen J. Spak; Olivier R. Martin

• Book ID: 104209750
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 191 KB
• Volume: 56
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(99)00923-0

✦ Synopsis

The synthesis of an O,C-trisaccharide, namely methyl O-b-d-glucopyranosyl-(134)-C-b-d-glucopyranosyl-(136)-a-dglucopyranoside, was achieved in 14 steps by way of the nitro-aldol coupling of hepta-O-acetyl-b-cellobiosylnitromethane and methyl 6-aldehydo-2,3,4-tri-O-benzyl-a-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 b-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.