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Molecules 2013, 18(7), 8524-8534; doi:10.3390/molecules18078524
Article

A Straightforward Diphenylmethyl Protection Method and Deprotection of Some Pyrimidine Nucleosides

 and
*
Medicinal Chemistry, Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, Leuven 3000, Belgium
* Author to whom correspondence should be addressed.
Received: 31 May 2013 / Revised: 10 July 2013 / Accepted: 16 July 2013 / Published: 18 July 2013
(This article belongs to the Special Issue Synthesis of Nucleosides, Nucleotides and Their Derivatives)
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Abstract

Benzhydryl protection of primary and secondary alcohols has been reported previously via reaction with metal alcoholates. Our aim was to find generally useful and very mild conditions for the alcoholic protection and deprotection of nucleosides with the diphenylmethyl group. This was accomplished for some pyrimidine nucleosides using PdCl2 as the transition metal catalyst, and with optimization yields of 70–90% have been achieved. A lack of solubility of other nucleosides hampers its more general use.
Keywords: hydroxyl protecting group; palladium catalyst; nucleoside; diphenyl methyl hydroxyl protecting group; palladium catalyst; nucleoside; diphenyl methyl
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Saudi, M.; van Aerschot, A. A Straightforward Diphenylmethyl Protection Method and Deprotection of Some Pyrimidine Nucleosides. Molecules 2013, 18, 8524-8534.

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