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Communication | Special issue | Vol 13, No. 1, 1979, pp.169-173
Published online, 1st January, 1970
DOI: 10.3987/S-1979-01-0169
The Synthesis of a Variety of Aminodeoxy-α-D-glycopyranosides by Way of a Novel Replacement Reaction

Raymond U. Lemieux,* Fawzy F. Z. Georges, and Zygfryd Smiatacz

*Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada


Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-oximino-α-D-arabino-hexopyranoside was found to undergo replacement of the 3-acetoxy group when reacted with nucleophilic reagents such as sodium azide, potassium phthalimide, sodium borohydride and sodium thiophenoxide. The resulting products could be transformed, depending on the reaction sequence, to 3-deoxy, 3,4-dideoxy, 3-amino-3-deoxy, 2-amino-2,3-dideoxy, 2,3-diamino-2,3-dideoxy, or 2-amino-2,3,4-trideoxy derivatives of an ethyl α-D-glycopyranoside.