Synthese der Epiminozucker

概要

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Two-step conversion of aldehydes to 2-monosubstituted aziridines has been extended to sugar derivatives. Treating O,O′-isopropylidene-D-glyceraldehyde with benzenesulfonyl chloride and sodium cyanide, 2-benzenesulfonyloxy-3,4-isopropylidenedioxybutyronitrile is obtained as a mixture of the diastereomers in a good yield, and is converted to the corresponding ketalaziridine, 2-(1,2-isopropylidenedioxyethyl)aziridine, by the reduction with lithium aluminum hydride. When the partially racemized isopropylideneglyceraldehyde is used, the diastereomers obtained are successfully separated by the fractional recrystallization. Each diastereomeric α-sulfonyloxynitrile is reduced by lithium aluminum hydride to afford the ketalaziridine, which is p-nitrobenzoylated and rearranged to the derivative of 1,3,4-trihydroxy-2-amino-butane by means of sodium iodide. Analogously, 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopentodialdo-1,4-furanose was converted to two urononitriles, 3-O-benzyl-5-O-benzenesulfonyl-1,2-O-isopropylidene-α-D-gluco-furanurononitrile and the epimeric β-L-idofuranurononitrile. The reduction of the former yielded 5,6-epimino-5,6-dideoxy-β-L-idofuranose.
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