Synthesis of a Natural Oligosaccharide Antibiotic Active against Helicobacter pylori

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• 作者：Shino Manabe ; Kazuyuki Ishii ; Yukishige Ito
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：August 3, 2007
• 年：2007
• 卷：72
• 期：16
• 页码：6107 - 6115
• 全文大小：213K
• 年卷期：v.72,no.16(August 3, 2007)
• ISSN：1520-6904

文摘

An oligosaccharide active against Helicobacter pylori was synthesized in a highly efficient manner forthe first time. The anti-H. pylori oligosaccharide structure is a core-2 branched-type oligosaccharidewith a characteristic -N-acetylglucosamine at the nonreducing end. The oligosaccharide was synthesizedfrom the nonreducing end to the reducing end, with an N-benzyl-2,3-oxazolidinone-carrying glycosyldonor used to introduce an -N-acetylglucosamine at the nonreducing end. Complete chemoselectiveactivation of a bromo sugar in the presence of a thioglycoside acceptor was achieved, and the use of2,6-dimethylphenyl thioglycoside prevented the aglycon transfer observed when the corresponding phenylthioglycoside is used as an acceptor.