Synthetic and mechanistic approaches to biologically potent aminoglycosides via diversified aziridination patterns
268 p.
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2011
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| Online Access: | https://hdl.handle.net/10356/47504 |
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sg-ntu-dr.10356-475042023-02-28T23:49:16Z Synthetic and mechanistic approaches to biologically potent aminoglycosides via diversified aziridination patterns Rujee Lorpitthaya Liu Xuewei School of Physical and Mathematical Sciences DRNTU::Science::Chemistry 268 p. The flexible installation of a sulfamate ester group on different positions of the glycal scaffold has been highlighted to be a new concept for synthesizing a- and P-aminoglycosides. The methodology incorporated three relevant steps: 1) the introduction of the sulfamate ester on the C3, C4, or C6 position of the glycal, 2) the intramolecular rhodium-catalyzed aziridination, and 3) regio- and stereoselective ring-opening of aziridines with readily available nucleophiles. With this rational design of substrates, the possibility, reactivity and limitation of forming aziridine-ring intermediates from 1, 2, and 3 have been performed based on the results from experimental observations and DFT calculations. DOCTOR OF PHILOSOPHY (SPMS) 2011-12-27T08:30:57Z 2011-12-27T08:30:57Z 2010 2010 Thesis Rujee Lorpitthaya. (2010). Synthetic and mechanistic approaches to biologically potent aminoglycosides via diversified aziridination patterns. Doctoral thesis, Nanyang Technological University, Singapore. https://hdl.handle.net/10356/47504 10.32657/10356/47504 Nanyang Technological University application/pdf |
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DRNTU::Science::Chemistry Rujee Lorpitthaya Synthetic and mechanistic approaches to biologically potent aminoglycosides via diversified aziridination patterns |
| description |
268 p. |
| author2 |
Liu Xuewei |
| author_facet |
Liu Xuewei Rujee Lorpitthaya |
| format |
Theses and Dissertations |
| author |
Rujee Lorpitthaya |
| author_sort |
Rujee Lorpitthaya |
| title |
Synthetic and mechanistic approaches to biologically potent aminoglycosides via diversified aziridination patterns |
| title_short |
Synthetic and mechanistic approaches to biologically potent aminoglycosides via diversified aziridination patterns |
| title_full |
Synthetic and mechanistic approaches to biologically potent aminoglycosides via diversified aziridination patterns |
| title_fullStr |
Synthetic and mechanistic approaches to biologically potent aminoglycosides via diversified aziridination patterns |
| title_full_unstemmed |
Synthetic and mechanistic approaches to biologically potent aminoglycosides via diversified aziridination patterns |
| title_sort |
synthetic and mechanistic approaches to biologically potent aminoglycosides via diversified aziridination patterns |
| publishDate |
2011 |
| url |
https://hdl.handle.net/10356/47504 |
| _version_ |
1759856247815798784 |