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Electronic Supplementary Information
Synthesis and glycosidase inhibition of conformationally locked DNJ and DMJ derivatives exploiting a 2-oxo-C-allyl iminosugar
Quentin Foucart,a Yuna Shimadate,b Jérôme Marrot,c Atsushi Kato,*b Jérôme Désiré,*a Yves Blériota*
a Université de Poitiers, UMR CNRS 7285, IC2MP, Équipe Synthèse organique, Groupe Glycochimie, 4 Rue Michel Brunet, 86073 Poitiers Cedex 9, France. b Department of Hospital Pharmacy, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan. c Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles, 45 Avenue des Etats-Unis, 78035 Versailles Cedex, France.
Copies of 1H and 13C NMR spectra p 2-54
Cristallographic data for compound 10b p 55-59
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2019
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1H NMR spectrum (CDCl3, 400 MHz) of compound 2b.
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13C NMR spectrum (CDCl3, 100 MHz) of compound 2b.
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1H NMR spectrum (CDCl3, 400 MHz) of compound 4.
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13C NMR spectrum (CDCl3, 100 MHz) of compound 4.
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1H NMR spectrum (CDCl3, 400 MHz) of compound 7.
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13C NMR spectrum (CDCl3, 100 MHz) of compound 7.
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1H NMR spectrum (CDCl3, 400 MHz) of compound 8a.
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13C NMR spectrum (CDCl3, 100 MHz) of compound 8a.
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2D NOESY 1H NMR spectrum (CDCl3, 400 MHz) of compound 8a.
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1H NMR spectrum (Acetone-d6, 400 MHz) of compound 8b.
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13C NMR spectrum (Acetone-d6, 100 MHz) of compound 8b.
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1H NMR spectrum (CDCl3, 400 MHz) of compound 9a.
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13C NMR spectrum (CDCl3, 100 MHz) of compound 9a.
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1H NMR spectrum (CDCl3, 400 MHz) of compound 9b.
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13C NMR spectrum (CDCl3, 100 MHz) of compound 9b.
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1H NMR spectrum (Methanol-d4, 400 MHz) of compound 10a.
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13C NMR spectrum (Methanol-d4, 400 MHz) of compound 10a.
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1H NMR spectrum (Methanol-d4, 400 MHz) of compound 10b.
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13C NMR spectrum (Methanol-d4, 400 MHz) of compound 10b.
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1H NMR spectrum (Acetone-d6, 400 MHz) of compound 11a.
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13C NMR spectrum (Acetone-d6, 100 MHz) of compound 11a.
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2D NOESY 1H NMR spectrum (Acetone-d6, 100 MHz) of compound 11a.
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1H NMR spectrum (Acetone-d6, 400 MHz) of compound 11a’.
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13C NMR spectrum (Acetone-d6, 100 MHz) of compound 11a’.
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1H NMR spectrum (Methanol-d4, 400 MHz) of compound 12a.
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13C NMR spectrum (Methanol-d4, 400 MHz) of compound 12a.
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1H NMR spectrum (Methanol-d4, 400 MHz) of compound 12a’.
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13C NMR spectrum (Methanol-d4, 400 MHz) of compound 12a’.
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1H NMR spectrum (CDCl3, 400 MHz) of compound 11b.
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13C NMR spectrum (CDCl3, 400 MHz) of compound 11b.
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2D NOESY 1H NMR spectrum (CDCl3, 100 MHz) of compound 11b.
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1H NMR spectrum (CDCl3, 400 MHz) of compound 11b’.
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13C NMR spectrum (CDCl3, 400 MHz) of compound 11b’.
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1H NMR spectrum (Methanol-d4, 400 MHz) of compound 12b.
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13C NMR spectrum (Methanol-d4, 400 MHz) of compound 12b.
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1H NMR spectrum (Methanol-d4, 400 MHz) of compound 12b’.
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13C NMR spectrum (Methanol-d4, 400 MHz) of compound 12b’.
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1H NMR spectrum (CDCl3, 400 MHz) of compound 13a.
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13C NMR spectrum (CDCl3, 100 MHz) of compound 13a.
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1H NMR spectrum (CDCl3, 400 MHz) of compound 13b.
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13C NMR spectrum (CDCl3, 100 MHz) of compound 13b.
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1H NMR spectrum (CDCl3, 400 MHz) of compound 14a.
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13C NMR spectrum (CDCl3, 100 MHz) of compound 14a.
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1H NMR spectrum (CDCl3, 400 MHz) of compound 14b.
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13C NMR spectrum (CDCl3, 100 MHz) of compound 14b.
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1H NMR spectrum (Methanol-d4, 400 MHz) of compound 15a.
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13C NMR spectrum (Methanol-d4, 400 MHz) of compound 15a.
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1H NMR spectrum (Methanol-d4, 400 MHz) of compound 15b.
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13C NMR spectrum (Methanol-d4, 400 MHz) of compound 15b.
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1H NMR spectrum (CDCl3, 400 MHz) of compound 17.
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13C NMR spectrum (CDCl3, 100 MHz) of compound 17.
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1H NMR spectrum (CDCl3, 400 MHz) of compound 19.
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13C NMR spectrum (CDCl3, 100 MHz) of compound 19.
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Cristallographic data for compound 10b
CCDC 1921458
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