First Gram-Scale Synthesis of a Heparin-Related Dodecasaccharide

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• 作者：Steen U. Hansen ; Gavin J. Miller ; Gordon C. Jayson ; John M. Gardiner
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：January 4, 2013
• 年：2013
• 卷：15
• 期：1
• 页码：88-91
• 全文大小：299K
• 年卷期：v.15,no.1(January 4, 2013)
• ISSN：1523-7052

文摘

The first example of a gram-scale synthesis of a structurally defined, heparin-related dodecasaccharide is reported. An iterative 14-step process using an iduronate donor disaccharide delivers >1g quantities of the dodecasaccharide sequence [GlcNS-IdoA2S]₆-OMe in 15% overall yield from the reducing terminal disaccharide, a 2 orders of magnitude increase in scale for access to synthetic heparanoid dodecasaccharide mimetics. The synthesis also delivers multigram amounts of the protected oligosaccharides from tetra- through to dodecasaccharide.