X-ray crystallography unequivocally confirmed the stereochemistry of the 2-C-methyl group in the title molecule, C10H16O6, in which the 1,5-lactone ring exists in a boat conformation. The use of d-galactose in the synthesis determined the absolute stereochemistry. The crystal exists as O—H⋯O hydrogen-bonded layers in the ab plane, with each molecule acting as a donor and acceptor for two hydrogen bonds.
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.
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