A new route to diverse 1-azasugars from N-Boc-5-hydroxy-3-piperidene as a common building block.
A new general method for the synthesis of a variety of 1-azasugars with a nitrogen atom at the anomeric position is described. The readily available chiral N-Boc-5-hydroxy-3-piperidene 3 is transformed to isofagomine (2), homoisofagomine (13), and 5'-deoxyisofagomine (14) via stereoselective epoxidation and regioselective ring-cleavage in a highly stereocontrolled manner. In addition, the synthesis of all four stereoisomers of 3,4,5-trihydroxypiperidines (18-21) classified as 1-azasugar-type glycosidase inhibitors was stereoselectively achieved from the (chiral) piperidene 3.
Ouchi
Hidekazu
H
Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, Sendai 981-8558, Japan.
Mihara
Yukiko
Y
Takahata
Hiroki
H
D001372:Aza Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D020650:Combinatorial Chemistry Techniques; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D050112:Imino Pyranoses; D015394:Molecular Structure; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000494:pharmacology; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D013237:Stereoisomerism
D001372:Aza Compounds; D004791:Enzyme Inhibitors; D050112:Imino Pyranoses; D009005:Monosaccharides; D010880:Piperidines; C098432:isofagomine; D006026:Glycoside Hydrolases