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

作者：Schombs Matthew W; Davis Ryan A; Fettinger James C; Gervay Hague Jacquelyn^*

来源：Acta Crystallographica Section C-Crystal Structure Communications, 2013, 69(9): 1062-+.

DOI：10.1107/S0108270113013723

• crystal structure
• neoglycoside

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

• 出版日期2013-9