141(P-98) セレノグリコシドを用いる新しいオリゴ糖の合成法(ポスター発表の部)

概要

論文の詳細を見る
Despite of the recent advances in the synthetic carbohydrate chemistry, efficient and rapid synthesis of oligosaccharides remains, a significant challenge. While a variety of chemoselective glycosylation strategies have received considerable interest for a rapid construction of oligosaccharides, it is highly desirable to develop a new glycosylation strategy by the use of single anomeric substituents as both the glycosyl donors and the acceptors for the generalized oligosaccharide synthesis. We report here a new strategy for the synthesis of oligosaccharides using selenoglycosides as both the glycosyl donors and the acceptors. The benzyl- and acetyl-protected arylselenoglycopyranoside reacted with Br_2 to give the corresponding 1-β-bromoglycoside in good yield with high β-selectivity (95-98%β). Due to the mild reaction conditions, the isomerization to the thermodynamically more stable α-isomer was very slow (>10% after 12h at room temperature). The bromoglycoside thus formed reacted with various glycosyl donors, including selenoglycosides, to give the desired glycosidation products in good to excellent yield. Since the products also possessed the arylselenyl group as the anomeric substituent, they could be directly used for the next glycosidation reaction. This sequential glycosidation strategy has been applied to the synthesis of hexa-saccharide by the exclusive use of the selenoglycosides. We believe that the current method provide a new entry for the more generalized oligosaccharide synthesis.
天然有機化合物討論会の論文
2000-10-01

141(P-98) セレノグリコシドを用いる新しいオリゴ糖の合成法(ポスター発表の部)

スポンサーリンク

概要

著者

関連論文

スポンサーリンク