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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

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

This work was supported by grants from the Spanish Ministerio de Economía y Competitividad (MINECO) (AGL2009-13255-C02-02/AGR and AGL2012-39880-C02-02)

Royal Society of Chemistry (RSC)

Manager: Ministerio de Ciencia e Innovación (Espanya)
Author: El Marrouni El Ghazaoui, Abdellatif
Heras i Corominas, Montserrat
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
This work was supported by grants from the Spanish Ministerio de Economía y Competitividad (MINECO) (AGL2009-13255-C02-02/AGR and AGL2012-39880-C02-02)
Document access: http://hdl.handle.net/2072/299089
Language: eng
Publisher: Royal Society of Chemistry (RSC)
Rights: Tots els drets reservats
Subject: Aminoàcids -- Síntesi
Amino acids -- Synthesis
Title: Synthesis of new unnatural Nα-Fmoc pyrimidin-4-one amino acids: use of the p-benzyloxybenzyloxy group as a pyrimidinone masking group
Type: info:eu-repo/semantics/article
Repository: Recercat

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