title: Highly Stereoselective Synthesis of Lamivudine (3TC) and Emtricitabine (FTC) by a Novel N-Glycosidation Procedure.
abstract: The combined use of silanes (Et3SiH or PMHS) and I2 as novel N-glycosidation reagents for the synthesis of bioactive oxathiolane nucleosides 3TC and FTC is reported. Both systems (working as anhydrous HI sources) were devised to act as substrate activators and N-glycosidation promoters. Excellent results in terms of chemical efficiency and stereoselectivity of the reactions were obtained; surprisingly, the nature of the protective group at the N4 position of (fluoro)cytosine additionally influenced the stereochemical reaction outcome.
authors.affiliation: †Dipartimento di Scienze Chimiche, Università degli Studi di Napoli Federico II, Via Cintia 21, 80126 Napoli, Italy.
authors.forename: Maria Federica
authors.initials: MF
authors.lastname: Caso
authors.affiliation: †Dipartimento di Scienze Chimiche, Università degli Studi di Napoli Federico II, Via Cintia 21, 80126 Napoli, Italy.
authors.forename: Daniele
authors.initials: D
authors.lastname: D'Alonzo
authors.affiliation: ‡Dipartimento di Farmacia, Università degli Studi di Napoli Federico II, Via D. Montesano 49, 80131 Napoli, Italy.
authors.forename: Stefano
authors.initials: S
authors.lastname: D'Errico
authors.affiliation: †Dipartimento di Scienze Chimiche, Università degli Studi di Napoli Federico II, Via Cintia 21, 80126 Napoli, Italy.
authors.forename: Giovanni
authors.initials: G
authors.lastname: Palumbo
authors.affiliation: †Dipartimento di Scienze Chimiche, Università degli Studi di Napoli Federico II, Via Cintia 21, 80126 Napoli, Italy.
authors.forename: Annalisa
authors.initials: A
authors.lastname: Guaragna
mesh_terms: D003841:Deoxycytidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000068679:Emtricitabine; D006031:Glycosylation; D019259:Lamivudine / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D003841:Deoxycytidine; D019259:Lamivudine; D000068679:Emtricitabine