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Facile preparation of the oxetane-nucleosides†
Małgorzata Bogucka,Petr Nauš,Wimal Pathmasiri,Jharna Barman,Jyoti Chattopadhyaya
Organic & Biomolecular Chemistry Pub Date : 11/07/2005 00:00:00 , DOI:10.1039/B511406C
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 β-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.

Graphical abstract: Facile preparation of the oxetane-nucleosides
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