Golgi endomannosidase inhibitor, alpha-D-glucopyranosyl-(1 --> 3)-1-deoxymannojirimycin: a five-step synthesis from maltulose and examples of N-modified derivatives.
Acid-catalysed O-acetylation of D-maltulose furnished the corresponding per-O-acetylated fructopyranose derivative that, after in situ deprotection at O-2 by reaction with triphenylphosphane dibromide, gave open-chain 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl-(1 --> 4)-1,3,5-tri-O-acetyl-6-bromo-6-deoxy-D-fructose. Standard deprotection employing sodium methoxide in methanol at -30 degrees C, followed by treatment of the resulting free 6-bromodeoxymaltulose with sodium azide in N,N-dimethylformamide, allowed access to 6-azidodeoxymaltulose. Hydrogenation over Pearlman's catalyst, accompanied by intramolecular reductive amination, yielded the desired title compound. This route allows access to preparative quantities and to a range of novel analogues with improved biostability.
Spreitz
Josef
J
Aglycon Company, Stremayrgasse 16, A-8010 Graz, Austria.
Stütz
Arnold E
AE
D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives* / Q000737:chemistry*; D002240:Carbohydrate Sequence; D002384:Catalysis; D004791:Enzyme Inhibitors / Q000494:pharmacology*; D005632:Fructose / Q000737:chemistry; D005960:Glucosides / Q000737:chemistry*; D006056:Golgi Apparatus / Q000201:enzymology* / Q000378:metabolism; D006859:Hydrogen / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008353:Mannitol / Q000737:chemistry; D008361:Mannosidases / Q000037:antagonists & inhibitors* / Q000737:chemistry*; D000432:Methanol / Q000737:chemistry / Q000494:pharmacology; D008956:Models, Chemical; D008969:Molecular Sequence Data; D011714:Pyrans / Q000737:chemistry; D013696:Temperature
D004791:Enzyme Inhibitors; D005960:Glucosides; D011714:Pyrans; C496679:glucopyranosyl-(1-3-)-1-deoxymannojirimycin; D017485:1-Deoxynojirimycin; D005632:Fructose; D008353:Mannitol; D006859:Hydrogen; D008361:Mannosidases; D000432:Methanol