The use of tri-O-acetyl-D-glucal and -D-galactal in the synthesis of 3-acetamido-2,3-dideoxyhexopyranoses and -hexopyranosides |
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Authors: | Liberek Beata Dabrowska Aleksandra Frankowski Ryszard Matuszewska Marlena Smiatacz Zygfryd |
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Institution: | Faculty of Chemistry, University of Gdańsk, Sobieskiego 18, PL-80-952 Gdańsk, Poland. |
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Abstract: | Addition of hydrazoic acid to alpha,beta-unsaturated aldehydes derived from tri-O-acetyl-D-glucal and -D-galactal gave 3-azido-2,3-dideoxyhexopyranoses. These were converted into 1,4,6-tri-O-acetyl-3-azido-2,3-dideoxyhexopyranoses as well as methyl and ethyl glycosides. Hydrogenation of the proamine group in 3-azido-2,3-dideoxy derivatives provided different 3-amino and 3-acetamido sugars. The configuration and conformation of all products were established on the basis of the 1H and 13 C NMR, IR and polarimetric data. |
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Keywords: | Hydrazoic acid 3-Azide-2 3-dideoxy sugar Hydrogenation 3-Amine-2 3-dideoxy saccharide AZT |
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