Synthetic study on α(2→8)-linked oligosialic acid employing 1,5-lactamization as a key step

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• 作者：Hidenori Tanaka ; Hiromune Ando ; Hideharu Ishida ; Makoto Kiso ; Hideharu Ishihara ; Mamoru Koketsu
• 关键词：Sialic acid ; Oligosialic acid ; Glycosylation ; Lactam
• 刊名：Tetrahedron Letters
• 出版年：2009
• 出版时间：5 August 2009
• 年：2009
• 卷：50
• 期：31
• 页码：4478-4481
• 全文大小：327 K

文摘

An attempt to synthesize α(2→8)-linked oligosialic acid utilizing a 1,5-lactamized sialyl acceptor is described. 1,5-Lactamization was experimentally proven to proceed only for α-sialoside, which was integrated into the synthetic cycle of oligosialic acid as a chemical sorting step to collect the desired α-sialoside and as a transformation step to produce a reactive sialyl acceptor for the next sialylation. Lactamized oligosialyl acceptors served as favorable coupling partners for sialylation, providing high stereoselectivities and high yields.