Research Article: 2-Azido-2-de­oxy-3,4-O-isopropyl­idene-2-C-methyl-d-talono-1,5-lactone

Date Published: May 01, 2010

Publisher: International Union of Crystallography

Author(s): Sarah F. Jenkinson, Ni Dai, George W. J. Fleet, David J. Watkin.


The relative stereochemistry of the title compound, C10H15N3O5, was confirmed by the crystal structure determin­ation. The absolute configuration was determined from the use of d-lyxonolactone as the starting material. The six-membered ring adopts a boat conformation with the larger azide group, rather than the methyl group, in the bowsprit position. In the crystal structure, a bifurcated inter­molecular O—H⋯O/O—H⋯N hydrogen bond links mol­ecules into chains running parallel to the b axis.

Partial Text

For carbohydrates as chirons, see: Lichtenthaler & Peters (2004 ▶); Fechter et al. (1999 ▶); Fleet (1989 ▶). For branched sugars and their use as chirons, see: Rao et al. (2008 ▶); Jones et al. (2008 ▶); Booth et al. (2008 ▶); Hotchkiss, Kato et al. (2007 ▶); da Cruz et al. (2008 ▶); Soengas et al. (2005 ▶). For the structures of similar sugars, see: Chesterton et al. (2006 ▶); Booth et al. (2007 ▶); Hotchkiss, Jenkinson et al. (2007 ▶); Baird et al. (1987 ▶); Bruce et al. (1990 ▶); Punzo et al. (2005 ▶). For the extinction correction, see: Larson (1970 ▶).




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