Benzyl (Bn) Type
Benzyl group is widely used as a protective group for hydroxy or amino group. Benzylation is usually accomplished by the Williamson ether synthesis under basic conditions. Fujifilm Wako Pure Chemical provides a new type of benzylation reagents that can react with alcohol even under neutral to acidic conditions.
In compared to the Williamson's method, TriBOT series are can be used under acidic conditions. Therefore, it is possible to utilize to unstable substrates under basic conditions. In the case of using DPT-BM, since the benzylation proceeds under neutral conditions, it can be applied to the compounds having various functional groups.
Both reagents are stable in the air and not irritant, in contrast to benzyl chloride and sodium hydride which are commonly used in the Williamson ether synthesis, so they can be handled easily.
Features
| Williamson synthesis | DPT-BM | TriBOT type | |
|---|---|---|---|
| conditions | basic | neutral | acidic |
| additive | NaH | MgO | organic acids |
| storage conditions | nitrogen blanket | freezer | ambient temp. & under air |
References
Yamada, K., Tsukada, Y., Karuo, Y., Kitamura, M. and Kunishima, M. : Chem. Eur. J., 20, 12274 (2014).
Yamada, K., Fujita, H. and Kunishima, M. : Org. Lett., 14 , 5026 (2012).
Yamada, K., Fujita, H., Kitamura, M. and Kunishima, M. : Synthesis, 45, 2989 (2013).
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