ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

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)