Synthesis of trehalose mimics by bismuth(III) triflate or bis(trifluoromethane)sulfonimide-catalyzed 1-C-methyl-d-hexopyranosylation

We investigated the ketopyranosylation of 2,3,4,6-tetra-O-benzyl-1-C-methyl-d-hexopyranoses with the benzylated d-aldohexopyranoses in order to produce novel non-reducing disaccharides as trehalose mimics. It was found that 5 mol % of bismuth(III) triflate or bis(trifluoromethane)sulfonimide efficiently catalyzed the ketopyranosylation that produced various non-reducing disaccharides.

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2,3,4,6-Tetra-O-benzyl-α-d-glucopyranosyl 2,3,4,6-tetra-O-benzyl-1-C-methyl-α-d-glucopyranosideC69H72O11[α]D23=+70 (c 2.0, CHCl3)Source of chirality: d-glucopyranose

2,3,4,6-Tetra-O-benzyl-α-d-mannopyranosyl 2,3,4,6-tetra-O-benzyl-1-C-methyl-α-d-glucopyranosideC69H72O11[α]D23=+59 (c 0.83, CHCl3)Source of chirality: d-glucopyranose and d-mannopyranose

2,3,4,6-Tetra-O-benzyl-α-d-galactopyranosyl 2,3,4,6-tetra-O-benzyl-1-C-methyl-α-d-glucopyranosideC69H72O11[α]D23=+74 (c 0.95, CHCl3)Source of chirality: d-glucopyranose and d-galactopyranose

2,3,4,6-Tetra-O-benzyl-β-d-galactopyranosyl 2,3,4,6-tetra-O-benzyl-1-C-methyl-α-d-glucopyranosideC69H72O11[α]D23=+48 (c 0.70, CHCl3)Source of chirality: d-glucopyranose and d-galactopyranose

2,3,4,6-Tetra-O-benzyl-α-d-glucopyranosyl 2,3,4,6-tetra-O-benzyl-1-C-methyl-α-d-mannopyranosideC69H72O11[α]D23=+57 (c 0.81, CHCl3)Source of chirality: d-glucopyranose and d-mannopyranose