| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1389436 | Carbohydrate Research | 2009 | 6 Pages |
Abstract
The acetolysis of several perbenzylated 6-deoxyhexose methyl glycosides under two mild conditions (10 equiv ZnCl2 in 2:1 v/v Ac2O–AcOH at 5 °C; 10:10:1 v/v/v Ac2O–AcOH–TFA at 70 °C) was studied. We focused on the effect of sugar configuration on the competition between mechanisms with activation at exocyclic or endocyclic oxygen site. No effect was detected in acetolysis using the TFA protocol promoting an exo-activation mechanism, which affords 1-O-Ac-pyranosides regardless of sugar configuration. On the contrary, it has a primary role in determining the endo- versus exo-product distribution on ZnCl2-promoted acetolysis.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Luigi Cirillo, Annalida Di Nola, Emiliano Bedini, Michelangelo Parrilli,