title: Facile preparation of the oxetane-nucleosides.
abstract: Efficient and practical large scale synthesis of suitably protected 1',2'-oxetane locked purine and pyrimidine nucleosides for incorporation in oligo-DNA or -RNA by solid-phase synthesis is reported. A high regio and stereoselectivity with preferential formation of the beta-anomer in the glycosylation reaction, using the Vorbrüggen procedure, was achieved by a convergent synthetic procedure with orthogonal protection strategy using either 1,2-di-O-acetyl-3,4-O-isopropylidene-6-O-(4-toluoyl)-d-psicofuranose or 2-O-acetyl-6-O-benzyl-1,3,4-tri-O-(4-toluoyl)-d-psicofuranose as the glycosyl donor.
authors.affiliation: Department of Bioorganic Chemistry, Box 581, Biomedical Center, University of Uppsala, S-75123 Uppsala, Sweden.
authors.forename: Małgorzata
authors.initials: M
authors.lastname: Bogucka
authors.forename: Petr
authors.initials: P
authors.lastname: Naus
authors.forename: Wimal
authors.initials: W
authors.lastname: Pathmasiri
authors.forename: Jharna
authors.initials: J
authors.lastname: Barman
authors.forename: Jyoti
authors.initials: J
authors.lastname: Chattopadhyaya
mesh_terms: D002241:Carbohydrates / Q000737:chemistry; D004988:Ethers, Cyclic / Q000737:chemistry*; D015394:Molecular Structure; D009705:Nucleosides / Q000737:chemistry*
chemical_list: D002241:Carbohydrates; D004988:Ethers, Cyclic; D009705:Nucleosides; C005287:oxetane