Access to 3-O-Functionalized N-Acetylneuraminic Acid Scaffolds

作者:Pascolutti Mauro; Madge Paul D; Thomson Robin J; von Itzstein Mark
来源:Journal of Organic Chemistry, 2015, 80(15): 7746-7751.
DOI:10.1021/acsjoc.5b00992

摘要

Direct access to 3-O-functionalized 2-alpha-Nacetylneurarninides and their corresponding 2,3-dehydro-2-deoxy-N-acetylneuraminic acid derivatives is described. Initially, a stereoselective ring-opening of the key intermediate N-acetylneuraminic acid (Neu5Ac) 2,343-epoxide with an alcohol provided the 3-hydroxy alpha-glycoside. O-Allcylation of the C3 hydroxyl group generated novel 3-O-functionalized Neu5Ac derivatives that provided the corresponding unsaturated derivatives upon elimination.

  • 出版日期2015-8-7

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