title: Synthesis of new unnatural N(α)-Fmoc pyrimidin-4-one amino acids: use of the p-benzyloxybenzyloxy group as a pyrimidinone masking group.
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 N(α)-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.
authors.affiliation: Department of Chemistry, Faculty of Science, University of Girona, Campus de Montilivi, E-17071 Girona, Spain. montserrat.heras@udg.edu.
authors.forename: Abdellatif
authors.initials: A
authors.lastname: ElMarrouni
authors.forename: Montserrat
authors.initials: M
authors.lastname: Heras
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis*; D001555:Benzene Derivatives / Q000737:chemistry*; D040761:Biomimetic Materials / Q000138:chemical synthesis*; D004952:Esters; D011744:Pyrimidinones / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C513120:4(3H)-pyrimidinone; D000596:Amino Acids; D001555:Benzene Derivatives; D004952:Esters; D011744:Pyrimidinones