Synthesis of D-ristosamine and its derivatives |
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Authors: | Istán Pelyvás Ferenc Sztaricskai László Szilágyi Rezsö Bognár József Tamás |
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Affiliation: | Research Group for Antibiotics, Hungarian Academy of Sciences, and Institute of Organic Chemistry, L. Kossuth University, H-4010 Debrecen Hungary;Central Chemical Research Institute, Hungarian Academy of Sciences, H-1088 Budapest Hungary |
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Abstract: | A convenient preparative route involving eleven steps starting from D-glucose is described for the synthesis of D-ristosamine (15) hydrochloride. Methyl 2-deoxy-β-D-arabino-hexopyranoside, prepared from 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex- 1-enitol, was benzylidenated, and the product mesylated to give methyl 4,6-O-benzylidene-2-deoxy-3-O-methylsulfonyl-β-D-arabino-hexopyranoside. Azidolysis of this compound and subsequent opening of the 1,3-dioxane ring with N-bromosuccinimide gave methyl 3-azido-4-O-benzoyl-6-bromo-2,3,6-trideoxy-βD-ribo-hexopyranoside. Simultaneous reduction of the azido and bromo groups gave a mixture that was benzoylated to give methyl N,O-dibenzoyl-β-D-ristosaminide and then hydrolyzed to 15 hydrochloride (3-amino-2,3,6-trideoxy-D-ribo-hexopyranose hydrochloride). |
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