Synthesis of N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids.
The synthesis of 10 N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids that are amenable to solid-phase synthesis is described. The general synthetic strategy involves initial incorporation of the protected amine, followed by selective TEMPO oxidation of C-6 hydroxyl groups to give the corresponding Fmoc-protected sugar amino acids. Amine incorporation may be accomplished from aminolysis of the free sugar or from glycosyl azide reduction. The reactions can be carried out on multigram scale, providing access to unique monomer units for future incorporation into combinatorial library syntheses.
Ying
Laiqiang
L
Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, CA 95616, USA.
Gervay-Hague
Jacquelyn
J
D020650:Combinatorial Chemistry Techniques; D020723:Glucuronic Acid / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure
D020723:Glucuronic Acid