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Issue 2, 1995
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Electrophilic azidation of 2-deoxy-aldono-1,5-lactones: an alternative route to 2-azido-2-deoxy-aldopyranoses

Abstract

Electrophilic azidation of tri-O-benzyl-2-deoxy-D-galactono-1,5-lactone 3 with triisopropylphenylsulfonyl azide, followed by selective reduction with diisobutylaluminium hydride, yielded tri-O-benzyl-2-azido-2-deoxy-D-galactopyranose 5 as the sole product in 80% yield, while the same sequence of reactions with the 2-deoxy-glucono-1,5-lactone derivative 8 afforded only tri-O-benzyl-2-azido-2-deoxy-D-mannopyranose 10 in 65% yield.

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Article type: Paper
DOI: 10.1039/C39950000221
J. Chem. Soc., Chem. Commun., 1995, 221-222

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    Electrophilic azidation of 2-deoxy-aldono-1,5-lactones: an alternative route to 2-azido-2-deoxy-aldopyranoses

    F. Dupradeau, S. Hakomori and T. Toyokuni, J. Chem. Soc., Chem. Commun., 1995, 221
    DOI: 10.1039/C39950000221

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