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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)

© Organic and Biomolecular Chemistry, 2015, vol. 13, núm. 3, p. 851-858

Royal Society of Chemistry (RSC)

Author: El Marrouni El Ghazaoui, Abdellatif
Heras i Corominas, Montserrat
Date: 2015
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)
Format: application/pdf
ISSN: 1477-0520 (versió paper)
1477-0539 (versió electrònica)
Document access: http://hdl.handle.net/10256/13672
Language: eng
Publisher: Royal Society of Chemistry (RSC)
Collection: MICINN/PN 2010-2012/ AGL2009-13255-C02-02
MICINN/PN 2013-2015/AGL2012-39880-C02-02
Reproducció digital del document publicat a: http://dx.doi.org/10.1039/C4OB02235A
Articles publicats (D-Q)
Is part of: © Organic and Biomolecular Chemistry, 2015, vol. 13, núm. 3, p. 851-858
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: DUGiDocs

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