Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 9 (September 2013)

organic compounds

Acta Cryst. (2013). C69, 1062-1066    [ doi:10.1107/S0108270113013723 ]

A fused [3.3.0]-neoglycoside lactone derived from glucuronic acid

M. W. Schombs, R. A. Davis, J. C. Fettinger and J. Gervay-Hague

Abstract: The bridged next-generation aminoglycoside (neoglycoside), 1-deoxy-1-[(methoxy)methylamino)]-2,5-di-O-triethylsilyl-[beta]-D-glucofuranurono-[gamma]-lactone {systematic name: (3S,3aS,5R,6R,6aS)-5-[methoxy(methyl)amino]-3,6-bis[(triethylsilyl)oxy]-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-2-one}, C20H41NO6Si2, was synthesized in a one-pot manner from commercially available D-glucuronic acid. This structure supports the properties associated with the anomeric effect for furanosides and can be employed to provide insight into the mechanisms by which alkoxyamine-appended natural products derive their enhanced biological activity. To the best of our knowledge, this is the first published crystal structure of a bicyclic neoglycoside and is the first neoglycoside to be completely and unambiguously characterized.

Formula: C20H41NO6Si2

Keywords: crystal structure; neoglycoside.

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[ doi:10.1107/S0108270113013723/eb5024sup3.pdf ]
experimental and NMR characterization data


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