Abstract
Does neighboring group participation actually enhance the reactivity of the anomeric center when the participating group is inherently disarming? To investigate the influence of the neighboring group effect from a 2-O protective group on acidic glycoside hydrolysis, 10 methyl glucosides having different protective groups on O2 have been synthesized and a clear trend between anomeric configuration, participation of the protective group, and the rate of hydrolysis could be observed.
| Original language | English |
|---|---|
| Journal | Organic Letters |
| Volume | 13 |
| Issue number | 22 |
| Pages (from-to) | 5956–5959 |
| Number of pages | 4 |
| ISSN | 1523-7060 |
| DOIs | |
| Publication status | Published - 18 Nov 2011 |