期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 19, 期 6, 页码 2168-2179出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201202374
关键词
carbohydrates; glycosidases; iminosugars; nitrogen heterocycles; reductive amination
资金
- ICSN
A series of novel polyhydroxylated N-alkoxypiperidines has been synthesized by ring-closing double reductive amination (DRA) of highly functionalized 1,5-dialdehydes with various hydroxylamines. The required saccharide-based dialdehydes were prepared efficiently from sodium cyclopentadienylide in seven steps. A two-step protocol has been developed for the DRA; it led, after deprotection, to isofagomine, 3-deoxyisofagomine, and numerous other N-alkoxy analogues. The barrier to inversion in these polyhydroxylated N-alkoxypiperidine derivatives was found by variable-temperature NMR methods to be approximately 15kcalmol1. With the exception of N-hydroxyisofagomine itself, none of the compounds prepared showed significant inhibitory activity against sweet almond -glucosidase.
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