AI Article Synopsis
- The study explores how DMAP (4-Dimethylaminopyridine) catalyzes the acetylation of octyl beta-D-glucopyranoside using various acetylating agents.
- The choice of counterion in the DMAP-acetyl complex significantly affects the reaction's efficiency, suggesting that how the transition state is deprotonated plays a key role.
- Noncovalent interactions between the acetate ion and the substrate appear to preferentially guide the acetylation to secondary hydroxyl groups.
Article Abstract
[reaction: see text] The DMAP-catalyzed acetylation of octyl beta-D-glucopyranoside with a series of acetylating agents has been investigated. The nature of the counterion of the catalytic DMAP-acetyl complex dramatically influences the outcome of the reaction, indicating that the deprotonation of the transition state is controlling the reaction. Noncovalent interactions of the acetate ion with the substrate seem to direct the acetylation toward secondary hydroxyl groups.
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| http://dx.doi.org/10.1021/ol0364935 | DOI Listing |
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