Utilization of nosylepimines of 1,6-anhydro-β-D-hexopyranoses for the preparation of halogenated aminosaccharides

  • Kroutil J
  • Karban J
  • Buděšínský M
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Abstract

The aziridine ring cleavage of N-nosylepimines 3 and 7 having D-allo and D-manno configurations with halides led regioselectively to N-o- nitrobenzenesulfonylated 2-halo-3-amino- and 3-halo-2-amino-2,3-dideoxy derivatives of 1,6-anhydro-β-D-glucopyranose 8-14 in 59-81% yields. Removal of o-nitrobenzenesulfonyl protecting group with benzenethiol afforded aminosaccharides, which were converted into more stable hydrochlorides 15-18. © 2003 Elsevier Ltd. All rights reserved.

Author-supplied keywords

  • Aziridines
  • NMR data
  • Nitrobenzenesulfonamides
  • Ring opening reactions
  • Stereospecific synthesis

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Authors

  • Jiří Kroutil

  • Jindřich Karban

  • Miloš Buděšínský

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