The usefulness of glycosyl iodides in carbohydrate chemistry has been demonstrated. Both anionic and neutral nucleophiles have been shown to react readily with glycosyl iodides as the glycosyl donor. High yields and stereoselectivity were obtained along with short reaction times. Anionic nucleophiles gave β glycosides selectively, whereas neutral nucleophiles gave α glycosides in the presence of tetrabutylammonium iodide. Initial investigation of the applicability of these glycosidation conditions to solid phase oligosaccharide synthesis has been accomplished.
| Identifer | oai:union.ndltd.org:arizona.edu/oai:arizona.openrepository.com:10150/282665 |
| Date | January 1998 |
| Creators | Hadd, Michael Joseph |
| Contributors | Gervay, Jacquelyn |
| Publisher | The University of Arizona. |
| Source Sets | University of Arizona |
| Language | en_US |
| Detected Language | English |
| Type | text, Dissertation-Reproduction (electronic) |
| Rights | Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author. |
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