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Issue 3, 2015
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Synthesis of new unnatural Nα-Fmoc pyrimidin-4-one amino acids: use of the p-benzyloxybenzyloxy group as a pyrimidinone masking group

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Abstract

The p-benzyloxybenzyloxy group is used to mask the oxo function of the 4(3H)-pyrimidinone ring in the synthesis of new unnatural amino acids. The synthetic approach is based on an aromatic nucleophilic substitution reaction between 4-[4-(benzyloxy)benzyloxy]-2-(benzylsulfonyl)pyrimidine and the nucleophilic side chain of several Nα-Boc amino esters, as the key step, followed by a series of standard protecting group transformations. p-Benzyloxybenzyloxy is efficiently removed under mild acid conditions to recover the 4(3H)-pyrimidinone system.

Graphical abstract: Synthesis of new unnatural Nα-Fmoc pyrimidin-4-one amino acids: use of the p-benzyloxybenzyloxy group as a pyrimidinone masking group

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Article information


Submitted
21 Oct 2014
Accepted
06 Nov 2014
First published
06 Nov 2014

Org. Biomol. Chem., 2015,13, 851-858
Article type
Paper

Synthesis of new unnatural Nα-Fmoc pyrimidin-4-one amino acids: use of the p-benzyloxybenzyloxy group as a pyrimidinone masking group

A. ElMarrouni and M. Heras, Org. Biomol. Chem., 2015, 13, 851
DOI: 10.1039/C4OB02235A

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