A new route to diverse 1-azasugars from N-Boc-5-hydroxy-3-piperidene as a common building block
| Autor: | Hiroki Takahata, Hidekazu Ouchi, Yukiko Mihara |
|---|---|
| Rok vydání: | 2005 |
| Předmět: |
Aza Compounds
Anomer General method Glycoside Hydrolases Molecular Structure Stereochemistry Chemistry Organic Chemistry Monosaccharides Regioselectivity Stereoisomerism Chemical synthesis Nitrogen atom Piperidines Combinatorial Chemistry Techniques Stereoselectivity Glycoside hydrolase Enzyme Inhibitors Imino Pyranoses |
| Zdroj: | The Journal of organic chemistry. 70(13) |
| ISSN: | 0022-3263 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|