Abstract

In this study, branched inner-core oligosaccharides of neisserial lipooligosaccharides was successively synthesized. We found that the glycosylation of a 4-O-substituted heptose derivative with a heptosyl donor proceeded smoothly proceeded in toluene and provided corresponding 3,4-di-O-substituted heptose as a single diastereomer. In addition, we found that the fragment condensation of a 3,4-di-O-substituded heptosyl donor with the axially oriented 5-position of a 4-O-substituted Kdo acceptor provided a consecutive branched hexasaccharide with a vicinal trans-diol of l-glycero-d-manno-heptose (Hep) and a vicinal cis-diol of 3-deoxy-d-manno-oct-2-ulosonic acid (Kdo) in its structure.

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