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

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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.

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Kroutil, J., Karban, J., & Buděšínský, M. (2003). Utilization of nosylepimines of 1,6-anhydro-β-D-hexopyranoses for the preparation of halogenated aminosaccharides. Carbohydrate Research, 338(24), 2825–2833. https://doi.org/10.1016/j.carres.2003.07.003

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