2013 年 71 巻 6 号 p. 616-624
1,2-cis amino glycosides are often found in biologically active oligosaccharides. For the stereoselective formation of 1,2-cis aminoglycosides, glycosyl donors with 2,3-trans carbamate group were developed. The first synthesis of anti-Helicobacter pylori oligosaccharide was achieved by using the novel glycosyl donor in an effective manner. Furthermore, the pyranosides with 2,3-trans carbamate groups were found to undergo endocyclic cleavage reactions, which are rarely found in pyranosides. The endocyclic cleavage reaction was confirmed both from experimental and computational approaches.
As an additional example of cooperative work of experimental and computational chemistry, understanding of the solvent effect in glycosylation reactions was also described.