This work describes the development of a protecting group for sulfate monoesters in carbohydrates. After initial trial studies, the trifluoroethyl ester was selected as a suitable protecting group. The ester was formed from the sulfate by treatment with trifluoro diazoethane. This protection method is shown to be compatible with other common protecting groups used in carbohydrate chemistry. The protecting group is proven to be stable to the manipulations of many other protecting groups. The utility of monosaccharides incorporating protected sulfate esters in synthesis has been examined. It has been proven that they are useful and versatile building blocks in the synthesis of more complex structures. Selective cleavage of the trifluoroethyl ester was achieved with potassium <I>tert</I>-butoxide. The mechanism for this deprotection reaction has been studied and this investigation has led to the advancement of alternative deprotection methods.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:660787 |
| Date | January 1999 |
| Creators | Proud, Andrew D. |
| Publisher | University of Edinburgh |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Source | http://hdl.handle.net/1842/12804 |
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