Double reductive amination of l-arabino-hexos-5-uloses: A diastereoselective approach to 1-deoxy-d-GALACTOSTATIN (cas 107537-94-0) derivatives☆

Add time:08/14/2019    Source:sciencedirect.com

The double reductive amination of l-arabino-hexos-5-ulose with benzhydrylamine and NaBH3CN takes place in a diastereospecific manner giving in moderate chemical yield (36 %) the galactosidase inhibitor 1-deoxy-d-galactostatin. The aminocyclization of 2,6-di-O-benzyl-l-arabino-hexos-5-ulose is more complicated giving results dependent from the type of amine: with ammonia or methylamine a mixture of C-5 epimeric 1-deoxyazapyranoses (d-galactol-altro ratio ≈ 4:1) is obtained in 45–65% combined yield, while with benzhydrylamine substantial amounts of an acyclic 1-deoxy-1-benzydrylamino-hexitol (10 % yield) is isolated together with the expected 1-deoxy-azasugars of the d-galacto and l-altro series.

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