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A simple access to the D-mannosidase inhibitor, 1-deoxymannojirimycin
Josef Spreitz1, Arnold E Stütz, Tanja M Wrodnigg
1Glycogroup, Institut für Organische Chemie der Technischen Universität Graz, Stremayrgasse 16, A-8010 Graz, Austria.
Abstract:
Crystalline 1,3,4,5-tetra-O-acetyl-6-bromo-6-deoxy-keto-D-fructose was prepared by reaction of 1,3,4,5-tetra-O-acetyl-D-fructopyranose with triphenylphosphane dibromide in dichloromethane. Subsequent deprotection followed by reaction of the free 6-bromodeoxyfructofuranose with sodium azide in N,N-dimethylformamide furnished the corresponding 6-azidodeoxyketose. Catalytic hydrogenation led to 1-deoxymannojirimycin in 27% overall yield from 1,3,4,5-tetra-O-acetyl-D-fructopyranose. This access is simple, inexpensive, high-yielding and clearly suitable for multigram preparations.