Facile preparation of the oxetane-nucleosides.
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.
Bogucka
Małgorzata
M
Department of Bioorganic Chemistry, Box 581, Biomedical Center, University of Uppsala, S-75123 Uppsala, Sweden.
Naus
Petr
P
Pathmasiri
Wimal
W
Barman
Jharna
J
Chattopadhyaya
Jyoti
J
D002241:Carbohydrates / Q000737:chemistry; D004988:Ethers, Cyclic / Q000737:chemistry*; D015394:Molecular Structure; D009705:Nucleosides / Q000737:chemistry*
D002241:Carbohydrates; D004988:Ethers, Cyclic; D009705:Nucleosides; C005287:oxetane