抄録
Trehalose has been widely found in nature, and its medical use is recently expected. We investigated the synthesis of several non-reducing disaccharides as trehalose mimics by the Lewis acid-promoted dehydrative glycosylation. The dehydrative glycosylation using 2,3,4,6-tetra-O-benzyl-D-glucopyranose was catalyzed by 20 mol% Bi(OTf)3 as the activator and the trehalose derivative was successfully obtained in good yield. Moreover, we investigated the synthesis of the trehalose mimics into which the 1-C-methyl-D-hexopyranose derivatives were incorporated.1 The 1-C-methyl-D-hexopyranosylation to several aldopyranoses was efficiently catalyzed in the presence of only 5 mol% Bi(OTf)3, and several kinds of trehalose mimics of non-reducing disaccharides were obtained in good yields. Our Bi(OTf)3-catalyzed dehydrative glycosylation was also applicable to the synthesis of glycosides using ordinary alcohols.
