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An Alternative Synthesis of Nojirimycin and Idonojirimycin

V. Sasinková and M. Koóš

Institute of Chemistry, Slovak Academy of Sciences, SK-842 38 Bratislava

 

Abstract: Starting from easily accessible 3-O-acetyl-5,6-dideoxy-1,2-O-isopropylidene-6-nitro-alpha-D-xylo-hex- 5-enofuranose, a five-step synthesis of nojirimycin (5-amino-5-deoxy-D-glucopyranose) and idonojirimycin (5-amino-5-deoxy-L-idopyranose) is described. For characterization and structure assignment, 1H  and 13C  NMR, EI and CI mass spectra of the prepared precursors were also studied. Nojirimycin and idonojirimycin were isolated and characterized via corresponding bisulfite addition products.

Full paper in Portable Document Format: 513a147.pdf

 

Chemical Papers 51 (3) 147–152 (1997)

Monday, June 24, 2024

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