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The bridged next-generation aminoglycoside (neoglycoside), 1-deoxy-1-[(methoxy)methylamino)]-2,5-di-O-triethylsilyl-β-D-glucofuranurono-γ-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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113013723/eb5024sup1.cif
CIF

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113013723/eb5024Isup2.hkl
structure factors

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108270113013723/eb5024sup3.pdf
experimental and NMR characterization data

CCDC reference: 964771


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