In my job I work with bent-core molecules, which have many aromatic rings with ester and biphenyl groups. And I use a benzylic group as a protecting group for one aromatic OH.
In the literature, the deprotection of this group to an OH takes place overnight. However, I require heating up to 50 °C or leaving the reaction for at least 3 days.
Why could this be?
The following paper might help u getting the reaction done in desired time.
A Fast and Effective Hydrogenation Process of Protected Penta saccharide: A Key Step in the Synthesis of Fondaparinux Sodium
- Organic Process Research & Development 17(5):869–875
- DOI 10.1021/op300367c
1. You must use high hydrogen pressure on a large scale of starting material (2g or more) for rapid hydrogenolysis.
2. Try working with a wet 50% Pd/C, dry Pd/C often fails.
3. An alternative method is to use lewis acids (FeCl3, TiCl4)
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