title: Synthetic approaches to a mononucleotide prodrug of cytarabine.
abstract: Synthetic pathways to a mononucleotide prodrug of cytarabine (Ara-C) bearing S-pivaloyl-2-thioethyl (tBuSATE) groups, as biolabile phosphate protections, are reported. Using a common phosphoramidite approach, two different kinds of nucleoside protecting groups have been investigated. During this study, we observed an intermolecular migration of the Boc protecting group in the course of the tert-butyldimethylsilyl ether cleavage using tetrabutyl ammonium fluoride.
authors.affiliation: UMR 5625 CNRS-UM II, Université Montpellier II, France.
authors.forename: R
authors.initials: R
authors.lastname: Bazzanini
authors.forename: M H
authors.initials: MH
authors.lastname: Gouy
authors.forename: S
authors.initials: S
authors.lastname: Peyrottes
authors.forename: G
authors.initials: G
authors.lastname: Gosselin
authors.forename: C
authors.initials: C
authors.lastname: Périgaud
authors.forename: S
authors.initials: S
authors.lastname: Manfredini
mesh_terms: D000964:Antimetabolites, Antineoplastic / Q000138:chemical synthesis*; D003561:Cytarabine / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D003854:Deoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D011355:Prodrugs / Q000138:chemical synthesis*
chemical_list: D000964:Antimetabolites, Antineoplastic; D003854:Deoxyribonucleotides; D011355:Prodrugs; D003561:Cytarabine