1 Sialyl-Lewis X (SLex)およびその類縁体の合成研究(口頭発表の部)

概要

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The cell surface-bound polysaccharide sialyl-Lewis X antigen (SLe^<X>1) was synthesized. We revealed that both D-glucal and D-lactal derivatives where only the primary alcohol functions were protected underwent regiospecific L-fucosylation at the allylic alcohol. In the Dlactal series D-sialylation occurred specifically at the C3 hydroxyl in the galactosyl domain. The conciseness of our route enabled us to produce gram quantities of 9. To overcome the difficulty in extending our sunlfonamideglycosylation methodology, stannyl alkoxide as a glycosyl acceptor was investigated. We demonstrate successful application of stannyl alkoxide addition to glycal-derived iodosulfonamides, resulting in the total synthesis of sialyl-Lewis X antigen (1) and synthesis of hexasaccharide 20.
天然有機化合物討論会の論文
1992-09-10