CARB 116 |
| Alkoxyamines (R-ONHR') react with unprotected reducing sugars under very mild conditions to form neoglycosides in excellent yields, and depending on the identity of the sugar, excellent stereoselectivities. This reaction has been used to form oligosaccharide analogs, glycopeptides, and most recently a library of "glycorandomized" natural products from which several anti-cancer agents were identified. Despite the utility of alkoxyamine-mediated neoglycosylation in the synthesis of biological active substances, little work has been done to explore the scope of this reaction or to address its limitations. A systematic exploration of how solvent and alkoxyamine substituents (R and R') influence the yield of neoglycosylation was carried out. These efforts led to the synthesis of previously inaccessible glycosides and allowed us to assess how neoglycosidic linkages influence the cytotoxicity of cardiac glycosides.
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Carbohydrate Chemistry and Biochemistry
8:30 AM-11:50 AM, Thursday, August 23, 2007 BCEC -- 162B, Oral
Division of Carbohydrate Chemistry |
