184017-41-2Relevant academic research and scientific papers
Practical route to D-manno and D-gluco azasugars from C2 symmetric bis-aziridines
McCort, Isabelle,Dureault, Annie,Depezay, Jean-Claude
, p. 7717 - 7720 (1996)
6-Amino-2,5-imino-D-glucitol 2 and 6-amino-1,5-imino-D-mannitol 3, substituted by a free hydroxyl group, have been synthesized from the conformationally flexible N-Boc bis-aziridine 1. Regioselective ring-opening of 1 by acetic acid is a straight way towards 2, while reaction of 1 with water or allylic alcohol under ytterbium triflate catalysis produces selectively the azapyranose 3. Nitrous deamination carried out on the cyclic carbamate-protected pyrrolidine 4 leads to a 1:1 mixture of both 2,5-imino-D-glucitols 5 and 6 bearing a free hydroxyl substituent either at C-1 or at C-6.
Synthesis and evaluation as glycosidase inhibitors of 2,5-imino-D- glucitol and 1,5-imino-D-mannitol related derivatives
McCort, Isabelle,Fort, Sebastien,Dureault, Annie,Depezay, Jean-Claude
, p. 135 - 143 (2007/10/03)
Selectively functionalized 2,5-imino-D-glucitol and 1,5-imino-D-mannitol derivatives were synthesized and tested as precursors of hydrolytically resistant pseudo-disaccharides. Among them N-acetyl-6-amino-6-deoxy-2,5- imino-D-glucitol (11) and N-acetyl-6-amino-6-deoxy-1,5-imino-D-mannitol (12) were found potent and specific inhibitors against β-D-glucosidase and α-L- fucosidase, respectively. (C) 2000 Elsevier Science Ltd.
