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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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