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A concise synthesis of the title trisaccharide is described in which the key β-mannosylation reaction is achieved directly, with high yield and selectivity, by triflic anhydride mediated coupling of S-ethyl 2-O-allyl-3-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thia-α-D-mannopyranoside S-(R)-oxide with methyl 2,3,6-tri-O-benzyl-α-D-glucopyranoside. After deallylation of the so-formed disaccharide, β-xylopyranosylation...
High yield, highly stereoselective methods for the synthesis of β-mannopyranosides of primary, secondary, and tertiary alcohols are presented. Activation of mannosyl sulfoxides or mannosyl thioglycosides with trifluoromethanesulfonic anhydride or benzenesulfenyl triflate, respectively, leads to the efficient formation of α-mannosyl triflates at -78 °C in dichloromethane, in the presence of 2,6-di-tert-butyl-4-methylpyridine...
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