title: A simple access to the D-mannosidase inhibitor, 1-deoxymannojirimycin.
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.
authors.affiliation: Glycogroup, Institut für Organische Chemie der Technischen Universität Graz, Stremayrgasse 16, A-8010 Graz, Austria.
authors.forename: Josef
authors.initials: J
authors.lastname: Spreitz
authors.forename: Arnold E
authors.initials: AE
authors.lastname: Stütz
authors.forename: Tanja M
authors.initials: TM
authors.lastname: Wrodnigg
mesh_terms: D017485:1-Deoxynojirimycin / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008361:Mannosidases / Q000037:antagonists & inhibitors*
chemical_list: D004791:Enzyme Inhibitors; D017485:1-Deoxynojirimycin; D008361:Mannosidases