A highly efficient synthesis of an octasaccharide, the repeating unit of the cell-wall mannan of Trichophyton mentagrophytes and T. rubrum.
A highly concise and effective synthesis of the mannose octasaccharide repeating unit of the cell-wall mannan of Trichophyton mentagrophytes and T. rubrum was achieved via 6-O-glycosylation of a tetrasaccharide acceptor with a tetrasaccharide donor, followed by deprotection. The key tetrasaccharide (11) was constructed by selective 6-O-glycosylation of allyl 3,4-di-O-benzoyl-alpha-D-mannopyranosyl-(1-->6)-2,3,4-tri-O-benzoyl-alpha-D-mannopyranoside with 6-O-acetyl-2,3,4-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate, then with 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate. The tetrasaccharide acceptor (13) was obtained by selective 6-O-deacetylation of 11, while the tetrasaccharide donor 12 was obtained by deallylation of 11, followed by trichloroacetimidation.
Ning
Jun
J
Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, PO Box 2871, 100085, Beijing, PR China.
Heng
Linsen
L
Kong
Fanzuo
F
D002240:Carbohydrate Sequence; D002473:Cell Wall / Q000737:chemistry*; D008351:Mannans / Q000737:chemistry*; D008362:Mannosides / Q000138:chemical synthesis* / Q000737:chemistry; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D014249:Trichophyton / Q000737:chemistry*
D008351:Mannans; D008362:Mannosides; D009844:Oligosaccharides