Scalable Synthesis of l-Iduronic Acid Derivatives via Stereocontrolled Cyanohydrin Reaction for Synthesis of Heparin-Related Disaccharides

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• 作者：Steen Uldall Hansen ; Marek Barth ; Bader A. B. Salameh ; Robin G. Pritchard ; William T. Stimpson ; John M. Gardiner ; Gordon C. Jayson
• 刊名：Organic Letters
• 出版年：2009
• 出版时间：October 15, 2009
• 年：2009
• 卷：11
• 期：20
• 页码：4528-4531
• 全文大小：193K
• 年卷期：v.11,no.20(October 15, 2009)
• ISSN：1523-7052

文摘

l-Ido cyanohydrin 3 was prepared from diacetone-d-glucose in four steps and 76% overall yield and 90% de via cyanohydrin reaction of aldehyde 2. This process can be scaled to provide >1 mol of pure l-ido cyanohydrin 3. Cyanohydrin 3 was elaborated to 1,2-isopropylidine-protected l-ido nitrile (8), iduronic amide 9, and known carboxy ester 10. Coupling of 8 and 9 with glucosamine donors leads to new types (6-cyano and 6-carboxamide) of heparin-related disaccharides.