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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El Marrouni El Ghazaoui, Abdellatif
orcId Heras i Corominas, Montserrat​ researcherId Heras i Corominas, Montserrat​ scopusId Heras i Corominas, Montserrat​ ​
Heras i Corominas, Montserrat
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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 ​
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