Synthesis of amino sugars via isoxazolines DL- and D-lividosamine (2-amino-2,3-dideoxy-ribo-hexose) derivatives from 4-vinyl-1,3-dioxolanes and nitroacetaldehyde acetals |
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Authors: | Volker Jäger Rudolf Schohe |
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Affiliation: | Institut für Organische Chemie der Universität Würzburg, Am Hubland, D-8700 Würzburg Federal Republic of Germany |
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Abstract: | 1,3-Dipolar cycloaddition of nitrile oxides, generated from nitroethanol and nitroacetaldehyde derivatives 3, 21 and 22, respectively, and of benzonitrile oxide to 4-vinyldioxolanes 1, 2 gave ca 4:1 erythro/threo mixtures of corresponding isoxazolines. LAH reduction of erytho isoxazolines proceeded with similar (ca 4:1) selectivity to furnish protected ribo-amino-polyols 11, 15,19, DL- and D-lividosamines 31 and 33, respectively, as main products. The DL-lividosamine derivative 33 was obtained pure by crystallization. In the D-series, the corresponding ribo/arabino mixture D-31/D-32 was transformed to the known α-methyl D-lividosaminide D-37. |
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