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Dr. Gaëlle Malik, Angélique Ferry, Dr. Xavier Guinchard, Dr. Thierry Cresteil and Prof. Dr. David Crich N[BOND]O Bond as a Glycosidic-Bond Surrogate: Synthetic Studies Toward Polyhydroxylated N-Alkoxypiperidines Chemistry - A European Journal 19

Article first published online: 19 DEC 2012 | DOI: 10.1002/chem.201202374

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NO glycosidic bonds: The synthesis of highly functionalized dialdehydes from sodium cyclopentadienylide is described. The dialdehydes undergo double reductive aminations with N-alkoxyamines for the synthesis of various N-alkoxypiperidines, which, after deprotection, furnish glycomimetics with an “anomeric” hydroxylamine as an achiral surrogate for the glycosidic bond (see scheme; Bn: benzyl; NAP: naphthylmethyl). The energy for the nitrogen inversion in these series is approximately 15 kcal mol−1, which theoretically enables molecular adaptability to biological targets.

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