A highly efficient synthesis of an octasaccharide, the repeating unit of the cell-wall mannan of Trichophyton mentagrophytes and T. rubrum
2002
Ning, J. | Heng, L.S. | Kong, F.Z.
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 leads to 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.
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