1 Supporting Information An approach to 8 stereoisomers of homonojirimycin from D-glucose via kinetic & thermodynamic azido-γ -lactones Andreas F. G. Glawar, a,b Sarah F. Jenkinson, b Scott J. Newberry, b Amber L. Thompson, c Shinpei Nakagawa, d Akihide Yoshihara, e Kazuya Akimitsu, f Ken Izumori, e Terry D. Butters, a Atsushi Kato* d and George W. J. Fleet* a,b a Oxford Glycobiology Institute, University of Oxford, South Parks Road, Oxford, OX1 3QU, United Kingdom. Fax: +44 (0)1865 275216; Tel: +44 (0)1865 275342; b Chemistry Research Laboratory, 12 Mansfield Road, Oxford, OX1 3TA, United Kingdom. Fax: +44 (0)1865 285002; Tel: +44 (0)1865 275645; E-mail: George.Fleet@chem.ox.ac.uk c Chemistry Research Laboratory, Department of Chemical Crystallography, University of Oxford, Mansfield Road, Oxford, OX1 3TA, United Kingdom. d Department of Hospital Pharmacy, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan; E-mail: kato@med.u-toyama.ac.jp e Rare Sugar Research Center, Kagawa University, 2393 Ikenobe, Miki-cho, Kita-gun, Kagawa 761-0795, Japan. f Faculty of Agriculture, Kagawa University, 2393 Ikenobe, Miki-cho, Kita-gun, Kagawa 761-0795, Japan. Table of Contents EXPERIMENTAL SECTION ON α-HOMONOJIRIMYCIN AND EPIMERS: .................................................................................. 2 X-RAY CRYSTALLOGRAPHY ON EPIMERIC AZIDO-LACTONES: ............................................................................................ 5 NMR SPECTRA OF SYNTHETIC COMPOUNDS: ............................................................................................................................ 6 REFERENCES: ..................................................................................................................................................................................... 25 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2013