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Carbohydr Res. 2002 Jul 16;337(13):1159-64.

A highly efficient synthesis of an octasaccharide, the repeating unit of the cell-wall mannan of Trichophyton mentagrophytes and T. rubrum.

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  • 1Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, PO Box 2871, 100085, Beijing, PR China.

Abstract

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.

PMID:
12110189
[PubMed - indexed for MEDLINE]
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