Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, Canada M5S 3H6.
J Org Chem. 2012 Sep 7;77(17):7401-10. doi: 10.1021/jo301240j. Epub 2012 Aug 14.
A versatile synthesis of orthogonally protected derivatives of carba-α-D-glucosamine, carba-α-D-mannose, carba-α-D-mannuronic acid, carba-β-L-idosamine, and carba-β-L-gulose from methyl α-D-mannoside is described. Our synthetic strategy utilizes the palladium-promoted Ferrier carbocyclization and persistent butane-2,3-diacetal protection to produce a key chiral cyclohexanone intermediate, from which all five carbasugar derivatives can readily be obtained.
本文描述了从甲基-α-D-甘露糖苷出发，对碳-α-D-葡萄糖胺、碳-α-D-甘露糖、碳-α-D-甘露糖醛酸、碳-β-L-艾杜糖胺和碳-β-L-呋拉糖的正交保护衍生物进行的多功能合成。我们的合成策略利用钯促进的 Ferrier 碳环化和持久的丁烷-2,3-二甲醇保护作用，生成关键的手性环己酮中间体，由此可以轻松获得所有五个碳糖衍生物。
