A simple access to the D-mannosidase inhibitor, 1-deoxymannojirimycin.
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.
Spreitz
Josef
J
Glycogroup, Institut für Organische Chemie der Technischen Universität Graz, Stremayrgasse 16, A-8010 Graz, Austria.
Stütz
Arnold E
AE
Wrodnigg
Tanja M
TM
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*
D004791:Enzyme Inhibitors; D017485:1-Deoxynojirimycin; D008361:Mannosidases