The synthesis of evernitrose and 3-epi-evernitrose |
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Authors: | Juji Yoshimura Masafumi Matsuzawa Ken-ichi Sato Yuli Nagasawa |
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Institution: | Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology, Nagatsuta, Midori-ku, Yokohama 227 Japan |
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Abstract: | Evernitrose (2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitro-L-arabino-hexopyranose) was synthesized from methyl 2,6-dideoxy-4-O-methyl-α-L-erythro-hexopyranosid-3-ulose (2) through introduction of an amino group attached to the tertiary branching carbon by the method of Bourgeois, and subsequent oxidation of the amino group by m-chloroperoxybenzoic acid to a nitro group. 3-Cyano-3-O-mesylation of 2 by Bourgeois's method gave exclusively the desired product having the L-ribo configuration; furthermore, the β anomer of 2 gave the L-ribo and L-arabino products in the ratio of 1:2. The latter compound was converted into 3-epi-evernitrose by a similar sequence of reactions. |
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