Acta Cryst. (2009). E65, o263  [ doi:10.1107/S1600536808044279 ]

7-Azido-N,N-diethyl-4,5-O-isopropylidene-4-C-methyl-3,6-anhydro-7-deoxy-D-glycero-D-manno-heptonamide

S. F. Jenkinson, C. Wang, M.-S. Pino-González, G. W. J. Fleet and D. J. Watkin

Abstract: The reaction of 5-azido-5-deoxy-2,3-O-isopropylidene-2-C-methyl-D-ribose with N,N-diethyl-2-(dimethylsulfuranylidene)acetamide gave the title compound, C₁₅H₂₆N₄O₅, as the major product arising from initial formation of an epoxide which was subsequently opened by intramolecular attack of the free 4-hydroxyl group. X-ray crystallography confirmed the relative stereochemistry of the title compound and the absolute configuration was determined by the use of D-ribose as the starting material. The crystal structure contains chains of molecules running parallel to the a axis, being linked by weak bifurcated O-H(N,N) hydrogen bonds.

Online 8 January 2009

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